- Rapid microwave-promoted catalyst- and solvent-free suzuki-type coupling reaction
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The catalyst- and solvent-free Suzuki coupling reaction of sodium tetraphenylborate with hypervalent iodonium salts was achieved under microwave irradiation in the absence of a base. A convenient method for formation of carbon-carbon bonds afforded good yields in a short time. Copyright Taylor & Francis Group, LLC.
- Yan, Jie,Hu, Weixiao,Zhou, Wei
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- Pd and Pd-CuO nanoparticles in hollow silicalite-1 single crystals for enhancing selectivity and activity for the Suzuki-Miyaura reaction
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Pd and Pd-CuO nanoparticles were successfully encapsulated in hollow silicalite-1 single crystals by tetrapropylammonium hydroxide (TPAOH) hydrothermal treatment with an "impregnation-dissolution-recrystallization" process. The size and number of particles in the hollow zeolite depended mainly on the nature of the metal. For palladium, the palladium nanoparticles easily aggregated into larger particles in the hydrothermal process, which displays excellent substrate selectivity for the meta- and para-substituted aryl bromides in the Suzuki-Miyaura reaction. For Pd-CuO binary metals (oxide), introducing copper oxide prevents aggregation of palladium, which shows about 3 times higher activity than encapsulated single Pd catalyst for the above reaction. The strategy using a hollow zeolite crystal as a support is a more reliable method for preparing multi-metallic (oxide) catalysts with well-dispersed nanoparticles.
- Dai, Chengyi,Li, Xinmin,Zhang, Anfeng,Liu, Chun,Song, Chunshan,Guo, Xinwen
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- Stainless steel mesh-GO/Pd NPs: Catalytic applications of Suzuki-Miyaura and Stille coupling reactions in eco-friendly media
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The immobilization of palladium nanoparticles (Pd NPs) on stainless-steel mesh is described in two short steps via deposition of graphene oxide (GO) on the stainless-steel mesh (mesh-GO) by electrophoretic deposition (EPD), preparation of Pd NPs using laser ablation in liquids (LAL) and finally the immobilization of Pd NPs on the mesh-GO by immersion in a Pd NP colloidal solution. The novel, efficient and reusable mesh-GO/Pd catalyst was characterized by various techniques such as SEM, EDS, UV-Vis and FT-IR spectroscopy and its catalytic activity was investigated for the Suzuki-Miyaura and Stille coupling reactions in ethanolic water.
- Feizi Mohazzab, Bahareh,Jaleh, Babak,Issaabadi, Zahra,Nasrollahzadeh, Mahmoud,Varma, Rajender S.
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- Antioxidant properties of synthesis nanometallic Pd-Ni?2-mercaptoethanol as effective catalyst for suzuki-miyaura reactions
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The palladium-catalyzed Suzuki coupling reaction is one of the most efficient strategies for constructing a carbon-carbon bond. In recent years, bimetallic catalysts have become candidates for the Suzuki coupling reaction. In this work, Pd-Ni?2-Mercaptoethanol nanoparticles were synthesized for the Suzuki-Miyaura cross-coupling of arylboronic acids with aryl bromides, in the N,N-dimethylformamide/water mixture catalyzed by Pd-Ni: A simple and efficient reaction performed in a solvent, without a ligand, and in open air. We found that the Suzuki-Miyaura reactions are remarkably fast (5 min), with high yields and the products are highly pure. The Pd-Ni?2-Mercaptoetanol nanoparticles have a narrow size distribution with a mean crystallite size of 10 nm. Radical scavenging activities of the complexes have been evaluated by using DPPH, DMPD+ and ABTS+ assays. IC50 values (μg/ml) of the complexes and standards on DPPH, DMPD+ and ABTS+ respectively following the sequences.
- Said, Khemais,Mesni, Ali,Salem, Ridha B.
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- Biosynthesis of supported Pd nanoparticles using poplar leaf as a reducing agent and carrier: A green route to highly efficient and reusable Suzuki coupling reaction catalyst
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A green process for the synthesis of supported Pd nanoparticles (NPs) using poplar leaf extract (PLE) as a reducing agent and the extracted residue of poplar leaf (RPL) as a carrier is reported. The Pd/RPL nanocomposites were characterized by XRD, TEM, SEM, EDS, XPS, FTIR, and ICP-AES. The spherical Pd NPs had a mean particle size of 3.1 nm and were evenly distributed on the RPL surface. More importantly, the Pd/RPL nanocomposites were used as a heterogeneous catalyst, which presented superior catalytic activity for the Suzuki coupling reaction. In addition, only a slight loss in the catalytic activity was observed after six recycles.
- Liu, Guanghui,Bai, Xuefeng,Lv, Hongfei
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- Highly active palladium nanoparticles immobilized on NH2-MIL-125 as efficient and recyclable catalysts for Suzuki-Miyaura cross coupling reaction
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Abstract Pd nanoparticles were deposited successfully on a porous metal-organic framework NH2-MIL-125, and characterized by powder X-ray diffraction, thermogravimetric analysis, N2 adsorption-desorption isotherms, X-ray photoelectron spectroscopy, and field emission transmission electron microscopy. The as-synthesized NH2-MIL-125-supported palladium nanoparticles exhibited excellent heterogeneous catalytic performance towards Suzuki cross coupling between the aryl chlorides and arylboronic acids. The catalyst could be reused at least four times under the optimized conditions with only a minor decrease in catalytic activity. The Sheldon test confirmed the heterogeneity of the catalyst.
- Puthiaraj, Pillaiyar,Ahn, Wha-Seung
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- Graphene-Supported Palladium Complex: A Highly Efficient, Robust and Recyclable Catalyst for the Suzuki-Miyaura Cross-Coupling of Various Aryl Halides
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We present a novel strategy based on the immobilization of a palladium complex on reduced graphene oxide for the development of a heterogeneous catalytic system with high efficiency and good recyclability. The prepared catalyst was tested for Suzuki-Miyaura cross-coupling reactions and shown to have a high catalytic efficiency, giving 83-98% conversion of the reactants under mild conditions. Moreover, it could be readily recycled and reused several times without significant loss of activity.
- Taher, Abu,Lee, Dong-Jin,Lee, Ik-Mo
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- Anchoring Pd(OAc)2 on amide-bonded covalent organic frameworks: An efficient heterogeneous Pd@OC-MA catalyst for Suzuki-Miyaura coupling reactions in water
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Nitrogen-rich of a melamine-based mesoporous covalent organic frameworks (COFs) materials were synthesized and used as a carrier to support a Pd(OAc)2. The Pd@OC-MA revealed an efficient catalytic activity and selectivity for Suzuki-Miyaura coupling reactions in an environmentally friendly water medium at room temperature. Specifically, it had moderate to excellent conversion for inactive chlorinated aromatic hydrocarbons. The catalyst was synthesized simply, had high stability and good selectivity, and was easy to recycle. Excellent catalytic activity of the Pd@OC-MA was also observed after five consecutive cycles.
- Wu, Shang,Zhang, Ying,Jiang, Hongyan,Wu, Lan,Ding, Ning,Jiang, Pengwei,Zhang, Hong,Zhao, Lianbiao,Yin, Fenping,Yang, Quanlu
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- Magnetically recoverable 2-(aminomethyl)phenols-modified nanoparticles as a catalyst for Knoevenagel condensation and carrier for palladium to catalytic Suzuki coupling reactions
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A class of magnetic nanoparticles modified by 2-(aminomethyl)phenols has been successfully designed and synthesized as a reusable catalyst for Knoevenagel reaction. What's more, such nanomaterial also proved as suitable carrier for immobilization of palladium nanoparticles and the obtained composite exerted potent catalytic activity in Suzuki coupling reactions. Both of the (aminomethyl)phenols-modified nanoparticles and its related palladium nanocatalyst could be easily separated and reused for several consecutive runs by magnetic decantation without significant loss of their catalytic efficiency.
- Wang, Gongshu,Ding, Zhiqiang,Meng, Lingxin,Yan, Guiyang,Chen, Zhangpei,Hu, Jianshe
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- Functionalization of fullerene (C60) with metformine to immobilized palladium as a novel heterogeneous and reusable nanocatalyst in the Suzuki-Miyaura coupling reaction at room temperature
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Pd supported on biguanide(metformine)-functionalized fullerene (C 60-Met/Pd2+) hybrid materials was fabricated for the first time. The catalyst prepared was characterized by X-ray diffraction spectroscopy (XRD), Fourier transform infrared (FT-IR), thermogravimetric analysis (TGA), and transmission electron microscopy (TEM). The catalyst showed excellent activity Suzuki-Miyaura coupling reaction of different aryl iodides and bromides with phenylboronic acid at room temperature in the EtOH:H2O (1:1) mixture as solvent. The yields of the products were in the range from 85% to 98%. The catalyst can be readily recovered and reused at least 6 consecutive cycles without significant loss in its catalytic activity. This is the new example for the development of fullerene (C60-Met-Pd) complexes which can be used as efficient recyclable catalysts without palladium leaching.
- Veisi, Hojat,Masti, Ramin,Kordestani, Davood,Safaei, Maryam,Sahin, Onur
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- Palladium nanoparticles supported on Layered Hydroxide Salts and their Use in Carbon-Carbon coupling organic reactions
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Palladium nanoparticles supported on zinc hydroxide salts were prepared by intercalation of [PdCl6]2- and its further reduction with ethanol under reflux. All the materials were completely characterized by atomic absorption spectroscopy (AAS), X-ray diffraction (XRD), thermogravimetric/ derivative thermogravimetric (TG/DTG) analyses, scanning electron microscopy (SEM), UV-Visible spectrometry and transmission electron microscopy (TEM). TEM analysis confirmed that the palladium nanoparticles were properly supported. The material containing supported palladium nanoparticles was used to promote Heck and Suzuki coupling reactions starting from aryl halides, with isolated yields of 98, 75 and 62percent of biphenyl, cinnamic acid and 3-nitrobiphenyl, respectively.
- Marti?nez, Maby,Ocampo, Rogelio,Rios, Luz Amalia,Rami?rez, Alfonso,Giraldo, Oscar
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- Pd@COF-QA: A phase transfer composite catalyst for aqueous Suzuki-Miyaura coupling reaction
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A Pd NP-loaded and paraffin-chain quaternary ammonium salt-decorated covalent organic framework, Pd@COF-QA, and its chitosan aerogel-based continuous flow-through reactor, which could be an excellent phase transfer catalyst to promote the aqueous Suzuki-Miyaura coupling reaction, is reported.
- Wang, Jian-Cheng,Liu, Cong-Xue,Kan, Xuan,Wu, Xiao-Wei,Kan, Jing-Lan,Dong, Yu-Bin
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- Polystyrene-Supported PPh3 in Monolithic Porous Material: Effect of Cross-Linking Degree on Coordination Mode and Catalytic Activity in Pd-Catalyzed C?C Cross-Coupling of Aryl Chlorides
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Hybridization of porous synthetic polymer and sophisticated ligands play an important role in transition-metal catalysis for chemical transformations at laboratory and industrial levels. A monolithic porous polymer, which is a single piece with continuous macropores, is desired for high permeability, fast mass transfer properties, high stability, and easy modification. Herein, we first develop a monolithic porous polystyrene containing three-fold cross-linked PPh3 (M-PS-TPP) for transition-metal catalysis. The monolithic and macroporous structure of M-PS-TPP was fabricated via polymerization-induced phase separation using porogenic solvent. Moreover, the M-PS-TPP was synthesized using different feed ratios of divinylbenzene (DVB) for site-isolation and mono-P-ligating behavior of PPh3. 31P CP/MAS NMR analysis revealed that the different selectivity of M-PS-TPPs was obtained in formation of mono-P-ligation toward PdII. The macroporous properties and controlled mono-P-ligating behavior of M-PS-TPP facilitated the challenging Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of chloroarenes.
- Matsumoto, Hikaru,Hoshino, Yu,Iwai, Tomohiro,Sawamura, Masaya,Miura, Yoshiko
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- Palladium nanoparticles supported on 1,3-dicyclohexylguanidine functionalized mesoporous silica SBA-15 as highly active and reusable catalyst for the Suzuki-Miyaura cross-coupling reaction
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This paper describes a simple procedure for the synthesis and application of SBA-15/1,3-DCG/Pd as a novel nano catalyst in Suzuki-Miyaura cross-coupling reactions under atmospheric conditions in aqueous media. The SBA-15/1,3-DCG/Pd is air and moisture stable and readily prepared and the results indicated that palladium nanoparticles (Pd NPs) with an average size of 10 nm were uniformly dispersed onto the inorganic support. Aryl halides, coupled with phenyl boronic acid, smoothly afford the corresponding cross-coupling products with good to excellent yields (83-99%). It was found that the catalytic system showed excellent activity for the Suzuki-Miyaura cross-coupling reaction of less reactive aryl chlorides with phenyl boronic acid. The reaction conditions have been evaluated considering the effect of various parameters such as reaction time, temperature, amount of catalyst, amount of base and its nature and solvent. The catalyst is completely recoverable in a facile manner from the reaction mixture and the efficiency of the nano catalyst remains unaltered even after five cycles. This journal is
- Veisi, Hojat,Amini Manesh, Abbas,Eivazi, Neda,Faraji, Ali Reza
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- Layered double hydroxide-supported nanopalladium: An efficient and reusable catalyst for Suzuki coupling of aryl iodides and bromides at room temperature
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Layered double hydroxide-supported nanopalladium (LDH-Pd0) is an effective catalyst for Suzuki cross-coupling of a wide range of aryl iodides and bromides with arylboronic acids at room temperature. The catalyst is reused for four cycles with consistent activity. Georg Thieme Verlag Stuttgart.
- Kantam, M. Lakshmi,Subhas,Roy, Sarabindu,Roy, Moumita
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- Incorporation of TiO2 coating on a palladium heterogeneous nanocatalyst. A new method to improve reusability of a catalyst
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To improve the reusability of a modified chitosan supported palladium catalyst (MC-Pd) it was coated with 50?wt% TiO2and in this way the MC-Pd@TiO2catalyst was prepared. The catalyst was characterized with different techniques. Activity of the catalyst was studied in the Suzuki cross-coupling reactions. The reusability of the catalyst was tested and the results indicated that after 10 runs, in the presence of MC-Pd catalyst the reaction yield decreased to 70% while it was 95% for the coated catalyst. After 10 runs, the Pd leached from MC-Pd catalyst was 20% and for the MC-Pd@TiO2 catalyst was less than 4%.
- Kamari, Younes,Ghiaci, Mehran
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- Nickel-glycerol: An efficient, recyclable catalysis system for Suzuki cross coupling reactions using aryl diazonium salts
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Nickel catalysed Suzuki reactions of phenyl boronic acids with aryl diazonium salts in glycerol as a reaction medium are reported. Various aryl diazonium salts were efficiently reacted with aryl boronic acids under optimized conditions to give the respective diaryl compounds in good to excellent yields. The base free conditions and use of glycerol as a solvent, which can be recycled successfully for up to five consecutive cycles, make the present protocol environmentally benign in nature.
- Bhojane, Jeevan Manohar,Sarode, Sachin Ashok,Nagarkar, Jayashree Milind
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- A novel and efficient coupling reaction of sodium tetraphenylborate with hypervalent iodonium salts
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The novel coupling reaction of sodium tetraphenylborate with hypervalent iodonium salts was achieved in acidic water, providing an efficient and rapid method for the formation of carbon-carbon bonds in excellent yield. Georg Thieme Verlag Stuttgart.
- Yan, Jie,Hu, Weixiao,Rao, Guowu
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- Synthesis of biguanide-functionalized single-walled carbon nanotubes (SWCNTs) hybrid materials to immobilized palladium as new recyclable heterogeneous nanocatalyst for Suzuki-Miyaura coupling reaction
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Pd supported on biguanide(metformine)-functionalized single-walled carbon nanotubes (SWCNT-Met/Pd2+) hybrid materials was fabricated for the first time. The prepared heterogeneous nanocatalyst was characterized by XRD, FT-IR, SEM, TGA and TEM. The catalytic activity of the prepared catalyst was investigated by employing Suzuki-Miyaura coupling reaction as a model reaction. A series of biphenyl compounds were synthesized through the Suzuki-Miyaura reaction using SWCNT-Met/Pd2+ as catalyst. The yields of the products were in the range from 80% to 95%. The catalyst can be readily recovered and reused at least 5 consecutive cycles without significant loss its catalytic activity.
- Veisi, Hojat,Khazaei, Ardeshir,Safaei, Maryam,Kordestani, Davood
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- An environmental catalyst derived from biological waste materials for green synthesis of biaryls via Suzuki coupling reactions
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Synthesis of bio-macromolecular supported catalysts has gained much recent attention due to their greener nature. Among the biopolymers, chitosan is widely used as a support material due to its high affinity for metal ions. In this study, chitosan-Ulva sp. (green alga) composite microbeads were prepared as a support material for palladium catalyst. Ulva sp. particles were incorporated into chitosan matrix to enhance the interaction with palladium ions. The catalytic performance of chitosan-Ulva supported Pd(II) catalyst was investigated in the synthesis of biaryls via the Suzuki coupling reaction. All the experiments were conducted without using any solvent under the microwave irradiation, which is also considered as a green technique. This green catalyst exhibited high selectivity and efficiency in the reactions of phenyl boronic acid with different aryl halides in only 4 min at low temperature (50 °C). Excellent TON and TOF values were achieved for the catalyst; 4950 and 75000. In addition, the catalyst did not lose its activity even after 8 cycles. It showed high thermal stability (216.8 °C) and durability in presence of oxygen. This green catalyst has a potential to be used in pharmacology, medicine and cosmetics.
- Baran, Talat,Sargin, Idris,Kaya, Murat,Mente?, Ayfer
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- Labile imidazolium salt protected palladium nanoparticles
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An imidazolium (Im) salt with two long alkyl substituents at N atoms is employed to prepare cubelike palladium nanoparticles (PdNPs). The bilayer nature of the capped Im salts is characterized by thermogravimetric analysis and NMR studies. These capped Im salts are labile, as evidenced by their displacement reaction with dimethylaminopyridine, and the observation of fast exchange between those free and capped Im salts on the NMR time scale. NMR results also show that these capped Im salts exhibit different diffusion rates, and interesting spinning rate dependent chemical shifts. These cubelike PdNPs could catalyze the Suzuki coupling of aryl chlorides and boronic acids with high yields in 10 min, even at room temperature.
- Lu, Jung-Tang,Lin, Joseph C. Y.,Lin, Meng-Che,Khupse, Nageshwar D.,Lin, Ivan J. B.
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- Active immobilized palladium catalyst based on multiporous amphiphilic graft copolymer
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Poly(vinylidene fluoride)-g-poly(dimethylaminoethyl methacrylate) (PVDF-g-PDMAEMA)/camphor system produces thermoreversible gel and leaching of camphor with cyclohexane yields amphiphilic multiporous material characterized from scanning electron microscopy (SEM), mercury intrusion porosimetry (MIP) and nitrogen adsorption porosimetry. Pd nanoparticles (Pd NPs, dia. 2.5-4.5 nm) are grown on this porous material by adsorption of Pd(OAc)2 followed by reduction with hydrazine. MIP and nitrogen porosimetry show that the xerogels are multiporous in nature and the pore size decreases in the Pd NPs captured sample. The BET surface area of the Pd NPs captured dried gel (24.3 m 2 g-1) is lower than that of pure gel (32.5 m2 g-1) due to the blocking of some pores by Pd NPs. The Pd NPs captured amphiphilic porous PVDF-g-PDMAEMA act as an effective catalyst for aerobic ligand free Suzuki coupling of aryl halides (X = I, Br and Cl) in aqueous medium.
- Samanta, Sanjoy,Layek, Rama K.,Nandi, Arun K.
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- Green synthesis of supported palladium nanoparticles employing pine needles as reducing agent and carrier: New reusable heterogeneous catalyst in the Suzuki coupling reaction
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A green method for the synthesis of supported Pd nanoparticles (NPs) using pine needle extract as the reducing agent and the extracted residue of pine needle (RPN) as the carrier is described. The Pd/RPN nanocomposites were characterized using Fourier transform infrared, UV–visible, inductively coupled plasma atomic emission and X-ray photoelectron spectroscopies, transmission electron microscopy and X-ray diffraction. The spherical Pd NPs had a mean particle size of 3.25?nm and were evenly distributed on the RPN surface. More importantly, the Pd/RPN nanocomposite, as a heterogeneous catalyst, presented superior catalytic activity for the Suzuki coupling reaction. The yield of the reaction of 4-bromotoluene with phenylboronic acid catalyzed by Pd0.03/RPN reached 98% with low Pd loading (0.1?mmol%) at room temperature for 30?min. In addition, the catalyst could be easily separated by centrifugation and reused at least six times without significant loss of activity.
- Liu, Guanghui,Bai, Xuefeng,Lv, Hongfei
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- Preparation of magnetic chitosan-supported palladium-5-amino-1H-tetrazole complex as a magnetically recyclable catalyst for Suzuki-Miyaura coupling reaction in green media
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The utilization of various tetrazoles as efficient ligands is a promising method for the functionalization of tetrazole-based heterogeneous catalysts. Their combination with magnetic species and natural supports exposes huge opportunities for the practical applications of heterogeneous catalysts. In this study, a green and novel strategy is applied to synthesize Fe3O4 magnetic nanoparticles (MNPs) incorporated with chitosan (CS) and 5-amino-1H-tetrazole with a long tail ((3-chloropropyl)trimethoxysilane) to immobilize palladium catalyst designated as Fe3O4–CS@tet-Pd(II). The prepared Fe3O4–CS@tet-Pd(II) was used as an efficient and magnetically recyclable catalyst for the Suzuki-Miyaura cross-coupling reaction (SMCR) using a mixture of EtOH/H2O as green media under aerobic conditions. All the expected products were obtained in high yields, indicating the high efficiency of this catalyst for the preparation of various biaryls by SMCR. Various latest techniques were used to characterize Fe3O4–CS@tet-Pd(II), e.g., Fourier-transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDS) elemental mapping, X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning TEM (STEM), high resolution TEM (HR-TEM), vibrating sample magnetometer (VSM), fast Fourier transform (FFT), thermogravimetric analysis (TGA), etc. This study presents a unique example of 5-amino-1H-tetrazole grafted on Fe3O4–CS, which can easily be separated using an external magnet and reused five times without significant decrease of catalytic activity. In addition, the introduced method has significant advantages such as the utilization of natural and inexpensive materials, easy work-up, high yields of products, and high catalytic activity.
- Bakhshali-Dehkordi, Raziyeh,Kamali, Taghi A.,Nasrollahzadeh, Mahmoud,Orooji, Yasin,Shokouhimehr, Mohammadreza
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- Nanocrystalline magnesium oxide-stabilized palladium(0): An efficient and reusable catalyst for Suzuki and stille cross-coupling of aryl halides
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A nanocrystalline magnesium oxide-stabilized palladium(0) catalyst is prepared by counterion stabilization of PdCl42- with nanocrystalline MgO followed by reduction. This ligand-free heterogeneous nanocrystalline MgO-stabilized nanopalladium [NAP-Mg-Pd(0)] catalyst using the basic MgO in place of basic ligands exhibits excellent activity in Suzuki and Stille cross-coupling of haloarenes (chloro, bromo and iodo) to afford the unsymmetrical biaryls. The catalyst is quantitatively recovered by simple filtration and reused for four cycles with almost consistent activity.
- Kantam, M. Lakshmi,Roy, Sarabindu,Roy, Moumita,Sreedhar,Choudary
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- Synthesis of bulky, electron rich hemilabile phosphines and their application in the Suzuki coupling reaction of aryl chlorides
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Novel electron rich, amine functionalised phosphines have been prepared and shown to belong to an unusual class of ligands that can activate palladium complexes to catalyse the Suzuki coupling reaction of chloroarenes.
- Clarke,Cole-Hamilton,Woollins
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- Palladium/phosphorus-functionalized porous organic polymer with tunable surface wettability for water-mediated Suzuki-Miyaura coupling reaction
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A series of phosphorus-functionalized porous organic polymers supported palladium catalysts with tunable surface wettability were successfully prepared using an easy copolymerization and successive immobilization method. The obtained polymers were carefully characterized by many physicochemical methods. Characterization results suggested that the prepared materials featured hierarchically porous structures, high pore volumes, tunable surface wettability and strong electron-donating ability towards palladium species. We demonstrated the use of these solid catalysts for water-mediated Suzuki-Miyaura coupling reactions. It was found that the surface wettability of the prepared catalysts has an important influence on their catalytic activities. The optimal catalyst, which has excellent amphipathicity and relatively high phosphorus concentration, displayed superior catalytic activity compared to the other catalysts. Under ambient conditions, a variety of aryl chlorides can be efficiently transformed to biaryls in high yields. Moreover, the catalyst could be easily recovered and reused at least six times.
- Lei, Yizhu,Chen, Zaifei,Li, Guangxing
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- Highly active and magnetically recoverable Pd-NHC catalyst immobilized on Fe3O4 nanoparticle-ionic liquid matrix for suzuki reaction in water
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Pd-NHC-ionic liquid matrix was immobilized into ionic liquid layers coated on the surface of Fe3O4. The immobilized Pd-NHC was used as a catalyst for Suzuki coupling. The catalyst exhibited both high catalytic activity and stability for the coupling between aryl bromide and arylboronic acid in water. This catalyst was simply recovered by an external permanent magnet and recycled without a significant loss in the catalytic activity.
- Taher, Abu,Jin-Beom Kim,Jung, Ji-Young,Ahn, Wha-Seung,Jin, Myung-Jong
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- Preparation and characterization of new palladium complex immobilized on (chitosan)/PoPD biopolymer and its catalytic application in Suzuki cross-coupling reaction
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The present work reports the design, synthesis, and characterization of palladium complex immobilized on chitosan/poly(o-phenylenediamine) (CS-PoPD-Pd) for the catalytic application in the Suzuki–Miyaura C-C cross-coupling reaction through a nontoxic, inexpensive, eco-friendly, and practical method. Fourier-transform–infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), elemental mapping, X-ray diffraction (XRD), and inductively coupled plasma-optical emission spectrometry (ICP-OES) techniques were used for analyzing the prepared catalyst. Characterization studies showed that CS-PoPD-Pd was successfully synthesized according to our design. CS-PoPD-Pd composite demonstrated high product yield and high turnover number (TON) and turnover frequency (TOF) values with small catalyst loading for the Suzuki–Miyaura C-C cross-coupling reaction under mild reaction conditions. Besides, the synthesized CS-PoPD-Pd composite could be readily recycled and reused for at least five runs without discernible loss of its catalytic activity.
- Seyedi, Neda,Zahedifar, Mahboobeh
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- Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold
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A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.
- Medina-Mercado, Ignacio,Porcel, Susana
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- 'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction
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An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is
- Ding, Chengrong,Guan, Chenfei,Miao, Huihui,Zhang, Guofu,Zhao, Yiyong
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supporting information
p. 3560 - 3564
(2022/03/07)
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- Fe3O4-SAHPG-Pd0 nanoparticles: A ligand-free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and C-H activation of pyrimidine cores
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This paper reports a green magnetic quasiheterogeneous efficient palladium catalyst in which Pd0 nanoparticles have been immobilized in self-assembled hyperbranched polyglycidole (SAHPG)-coated magnetic Fe3O4 nanoparticles (Fe3O4-SAHPG-Pd0). This catalyst has been used for effective ligandless Pd catalyzed Suzuki–Miyaura coupling reactions of different aryl halides with substituted boronic acids at room temperature and in aqueous media. Herein, SAHPG is used as support; it also acts as a reducing agent and stabilizer to promote the transformation of PdII to Pd0 nanoparticles. Also, this environmental friendly quasiheterogeneous catalyst is employed for the first time in the synthesis of new pyrimido[4,5-b]indoles via oxidative addition/C-H activation reactions on the pyrimidine rings, which were obtained with higher yield and faster than when Pd(OAc)2 was used as the catalyst. Interestingly, the above-mentioned catalyst could be recovered in a facile manner from the reaction mixture by applying an external magnet device and recycled several times with no significant decrease in the catalytic activity.
- Azizollahi, Hamid,Eshghi, Hossein,García-López, José-Antonio
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- Polydopamine-Encapsulated Dendritic Organosilica Nanoparticles as Amphiphilic Platforms for Highly Efficient Heterogeneous Catalysis in Water
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Aqueous heterogeneous catalysis is a green, sustainable catalytic process that attracts increasing attention, but it often suffers from poor mass transfer, substrate adsorption and catalyst dispersion. Herein, we synthesized a type of amphiphilic core-shell catalysts with a hydrophilic polydopamine (PDA) shell and a hydrophobic dendritic organosilica nanoparticle (DON) core for heterogeneous catalysis in water. The hydrophilic shell allowed the catalyst dispersing well in water, and the hydrophobic core facilitated the absorption of organic reactants. The hierarchical core-shell structure facilitated rational arrangement of the location of catalytic species to match the reaction sequence. The obtained metal, enzyme and metal-enzyme amphiphilic catalysts demonstrated improved stability, selectivity and activity in aqueous reactions, including Pd-catalyzed cross-couplings (Suzuki, Liebeskind-Srogl, Heck and Sonogashira), enzymatic enantioselective reduction, chemoenzymatic cascade synthesis of chiral compounds and chemoenzymatic cascade degradation of organophosphates. The amphiphilic catalysts could be easily in situ recovered, and their high catalytic performance was sustained for five cycles.
- Gao, Jing,Guo, Na,Jiang, Yanjun,Liu, Guanhua,Liu, Pengbo,Liu, Yunting,Wang, Zihan,Zhang, Lei
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supporting information
p. 1975 - 1982
(2021/06/09)
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- Synthesis of new adamantyl-imine palladium(II) complexes and their application in Mizoroki-Heck and Suzuki-Miyaura C[sbnd]C cross-coupling reactions
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Improving carbon–carbon cross-coupling reactions is an ongoing process and finding the most versatile and stable catalyst precursors has been of great interest. Ligand design has been proven to be important since it is responsible for providing electron density and steric saturation around the metal centre, thus contributing towards the stereo-electronic properties. The adamantyl moiety has been used to generate highly bulky and electron-rich ligands for application in palladium-catalysed cross-coupling reactions. Accordingly, we have prepared some Schiff-base adamantyl ligands (L1-L3) and complexed them with [PdCl2(MeCN)2] to afford the (pre)catalysts C1-C3, which were successfully applied in Mizoroki-Heck and Suzuki-Miyaura carbon–carbon cross-coupling reactions. The cross-coupling reaction products were obtained in good yields using 0.5 mol % Pd catalyst loading. C2 and C3 showed remarkable activity in the Mizoroki-Heck coupling reactions involving substrates with substituents on the olefin and aryl halide (including 4-Cl, 4-CH3, -CO2Me and -CO2Et). We also, observed that the Suzuki-Miyaura cross-coupling system was active towards challenging activated and deactivated aryl chlorides, with to up 70% conversions recorded. The mercury poisoning tests conducted revealed that the catalysts act as homogenous molecular active species in the Mizoroki-Heck reactions and act as both homogenous and heterogeneous catalysts in the Suzuki-Miyaura cross-coupling reactions.
- Makhubela, Banothile C. E.,Matsheku, Asanda C.,Maumela, Munaka C.
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- Pd/Cu-Free Cobalt-Catalyzed Suzuki and Heck Using Green Bio-Magnetic Hybrid and DFT-Based Theoretical Study
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Abstract: Several highly efficient and magnetically recyclable cobalt catalytic systems were prepared using magnetic chitosan and some safe and available organic compounds (Co-ligand@MNPs/Ch). The structure of these nanocomposites was confirmed by various physicochemical techniques such as FT-IR, XRD, TGA, VSM, TEM, SEM, CHNS and ICP-OES. These nano composites exhibit remarkable catalytic efficiency for Suzuki and Heck cross-coupling reactions in mild and green reaction conditions. The facile accessibility of starting materials, possible performance in air and eco-friendly conditions are merits of our catalysts. In addition, to describe and go insight to role and effect of ligands present in these catalysts, electrostatic interactions, density functional theory (DFT) model in molecular method were employed. Graphic Abstract: [Figure not available: see fulltext.]
- Hajipour, Abdol R.,Khorsandi, Zahra,Ahmadi, Mehnoosh,Jouypazadeh, Hamidreza,Mohammadi, Bahareh,Farrokhpour, Hossein
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p. 2842 - 2850
(2021/02/01)
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- An easily fabricated palladium nanocatalyst on magnetic biochar for Suzuki-Miyaura and aryl halide cyanation reactions
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Biochar is a carbon-rich solid, the surface of which is covered with a high density of functional carbonyl, hydroxyl and carboxylic acid groups. In this work, palladium nanoparticles were embedded on magnetic biochar and a new reusable and environmentally-friendly catalyst was developed and applied for the promotion of Suzuki-Miyaura C-C coupling and cyanation reactions. The high-carbon (77%), low-ash content (5.8%) and the relatively high surface area (266 m2g?1) of pine tree biochar (PTB) suggested that it might be highly suitable as a catalyst substrate. The Fe3O4-Pd-biochar nanocomposite was successfully characterized using SEM, TEM, EDX, FT-IR, BET and XRD. Its catalytic role was initially evaluated usingp-NO2C6H4I as a model reactant (for both types of reactions) and later for the production of biaryls and benzonitriles from a wide range of aryl halides under mild reaction conditions. Biaryls and benzonitriles were characterized using GC-MS. In the case of the Suzuki-Miyaura reaction, the optimum yield of 98% was obtained with a catalyst concentration of 0.04 mol%, microwave irradiation of 400 W, and a residence time of 5 min, using K2CO3as the base. With respect to the cyanation reaction, dimethylformamide, Na2CO3and 6 h were the optimum solvent, base and reaction duration, respectively. Subsequently, the nanocatalyst showed excellent catalytic activity in both reactions, achieving >88% yields in most cases, regardless of the aryl iodide or bromide used and the type of substitution.
- Turun?, Ersan,Akay, Sema,Baran, Talat,Kalderis, Dimitrios,Tsubota, Toshiki,Kayan, Berkant
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p. 12519 - 12527
(2021/07/25)
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- Magnetic covalently immobilized nickel complex: A new and efficient method for the Suzuki cross-coupling reaction
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In this study, an efficient procedure was reported to prepare Fe3O4@SiO2 magnetic nanoparticles (MNPs) with immobilized nickel NPs. In order to increase the activity of this catalyst, creatine as a ligand with high content of nitrogen atoms was linked onto the magnetic core–shell structure. Then, Ni(II) ions were coordinated on the surface of the silica-coated MNPs and reduced to Ni(0) NPs to obtain the final catalyst. The catalytic activity of the prepared catalyst was studied for the synthesis of biaryl derivatives via the Suzuki–Miyaura cross-coupling reaction in high yields. The catalyst could also be recovered and reused with no loss of activity over five successful runs.
- Keyhaniyan, Mahdi,Khojastehnezhad, Amir,Eshghi, Hossein,Shiri, Ali
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- Silica-coated magnetic nanoparticles functionalized cobalt complex: a recyclable and efficient catalyst for the C?C bond formation
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In this study, the Co-based catalyst was prepared by cobalt immobilization on the surface of functionalized silica-coated magnetic NPs (Fe3O4@SiO2-CT-Co) as a magnetically core–shell nanocatalyst and characterized by FT-IR, TGA, XRD, VSM, SEM, TEM, EDX, EDX mapping, and ICP techniques and appraised in the Suzuki–Miyaura cross-coupling reaction under mild reaction conditions. The results displayed the superparamagnetic behavior of the Fe3O4 NPs core encapsulated by SiO2 shell, and the size of the particles was estimated about 30?nm. Compared with the previously reported catalysts, the engineered Fe3O4@SiO2-CT-Co catalyst provided perfect catalytic performance for the Suzuki–Miyaura cross-coupling reaction in water as a green solvent and it was much cheaper in the comparison with the traditional Pd-based catalysts. Importantly, the durability of magnetic nanocatalyst was studied and observed that it is stable under the reaction conditions and could be easily reused for at least six successive cycles without any significant decrease in its catalytic activity. Graphic abstract: [Figure not available: see fulltext.]
- Haqjow, Hanif,Raoufi, Farveh
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p. 4113 - 4128
(2021/07/26)
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- Pd(II) complexes with ONN pincer ligand: Tailored synthesis, characterization, DFT, and catalytic activity toward the Suzuki-Miyaura reaction
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A pincer type ONN tridentate Schiff base ligand, 2-(((pyridin-2-yl)methylimino)methyl)-6-methoxyphenol, (L1) synthesized by the condensation of 4-hydroxy-3-methoxy-benzaldehyde and (pyridin-2-yl)methanamine. The ligand L1 and the new Pd(II) heteroleptic complexes of the composition [Pd(L1)(L2)]Cl, where L2 = benzimidazole, imidazole, benzooxazol or pyridine were synthesized and characterized by a set of chemical, spectrometric and spectroscopic analyses. These complexes were named 1 to 4, respectively. The FT-IR and DFT have suggested that ligand is coordinated with metal through azomethine-N and phenolic-O and arranged in square planar fashion around the metal. Correlation coefficients value between 0.995 - 0.993 shows satisfactory agreement in theoretical and experimental 1H-NMR and 13C-NMR. Benzimidazole anchored complex 1 exhibits an excellent catalytic activity. DFT calculated the energy profile diagram of the Suzuki-Miyaura reaction.
- Bagri, Sanjay Singh,Chaurasia, Bhaskar,Gaur, Pratiksha,Mehrotra, Ripul,Raidas, Mohan Lal,Shukla, Satyendra Nath
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- Pd(OAc)2-biuret: A highly efficient, low cost and phosphine-free catalyst system for biaryl synthesis under aerobic conditions at room temperature
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A highly efficient, less expensive and phosphine-free protocol for the Suzuki-Miyaura cross-coupling reactions of aryl halides and aryl boronic acids in iPrOH-H2O solvent under aerobic conditions has been developed. The results demonstrate that the biuret played a crucial role and making this protocol highly efficient. The Pd(OAc)2-biuret system exhibited superb catalytic activity towards the Suzuki-Miyaura cross-coupling reaction of a wide range of aryl halides with aryl boronic acids at room temperature, giving high yields even under very low catalytic loading. This system offers an attractive alternative to the existing protocols since the reaction proceeds in green solvent at room temperature with working simplicity, shorter reaction time, cost-effectiveness and provides the desired products in high yields. The effect of solvent, base as well as catalyst loading on the cross-coupling reaction of aryl halide with arylboronic acid is also described.
- Saikia, Bishwajit
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- Magnetic nanoparticles supported N-heterocyclic palladium complex: Synthesis and catalytic evaluations in Suzuki cross-coupling reaction
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Because of the robustness and magnetic properties, the magnetic materials are promising and alternative candidate for the fabrication of noble metal in chemical catalysis from the viewpoint of green chemistry. Accordingly, an eco-friendly magnetic palladium catalyst loaded on N-Methylimidazole functionalized Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2-NMIM-Pd) has been designed and prepared in the present work. The resultant composite exhibited excellent catalytic activity towards the Suzuki cross-coupling reaction for the synthesis of the corresponding biaryls in good to excellent yields (up to 96%) under aerobic conditions. In particular, this catalyst could be easily recovered through magnetic separation in a few cycles. The as-prepared palladium complex showed advantages including high thermal stability, low toxicity, moisture and oxygen insensitivities in Suzuki reactions. More importantly, this study presents a catalysis system, which will provide the magnetic materials access to the potential applications in a wide range of green organic catalysis.
- Dong, Yahao,Xue, Fengjun,Wei, Yuping
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- Agro-Waste Generated Pd/CAP-Ash Catalyzed Ligand-Free Approach for Suzuki–Miyaura Coupling Reaction
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Abstract: We converted agro-waste Custard Apple Peels (CAP) to ash via thermal treatment, on which Pd(OAc)2 was immobilized easily that produced a low-cost, highly efficient Pd/CAP-ash catalyst. The prepared catalyst was fully characterized by using FT-IR, SEM, EDX, XRF, DSC-TGA, BET, HR-TEM, and XPS techniques. The Pd/CAP-ash catalyst was conveniently applied for the Suzuki–Miyaura coupling reaction under external base free and ligand-free conditions in an aqueous-organic solvent to produce biphenyls in good to excellent yields. The main attraction of our protocol an application of palladium-supported agro-waste material which is easily recoverable and recyclable provides mono and bis-coupled derivatives in a short reaction time. Graphic Abstract: [Figure not available: see fulltext.].
- Patil, Rupesh C.,Jagdale, Ashutosh A.,Patil, Uttam P.,Ghodake, Jeevan S.,Mali, Sawanta S.,Hong, Chang K.,Patil, Suresh S.
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supporting information
p. 3617 - 3631
(2021/04/02)
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- Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
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A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.
- Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
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p. 9561 - 9568
(2021/08/06)
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- Synthesis of Enaminone-Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki-Miyaura Cross Coupling Reaction
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A series of Pd(II)-enaminone complexes, termed Pd(eao)2, have been synthesized and characterized. The investigation on the catalytic activities of these new Pd(II)-reagents has proved that the Pd(eao)2-1 possesses excellent catalytic activity for the Suzuki- Miyaura cross coupling reactions of aryl bromides/chlorides with aryl/vinyl boronic acids in the environmentally benign media of aqueous PEG400 at low loading (5 mol‰). The superiority of this Pd(II)-reagent to those commercial Pd(II) and Pd(0) catalysts in catalyzing the reactions has been confirmed by parallel experiments. What's more, Pd(eao)2-2 has been found as a practical catalyst for the homo-coupling reactions of aryl boronic acids.
- Fu, Leiqing,Cao, Xiaoji,Wan, Jie-Ping,Liu, Yunyun
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p. 254 - 258
(2020/01/25)
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- L-lysine-Pd Complex Supported on Fe3O4 MNPs: a novel recoverable magnetic nanocatalyst for Suzuki C-C Cross-Coupling reaction
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In this work, L-lysine-Pd Complex, immobilized onto the surface of Fe3O4 MNPs, was successfully prepared via simple and inexpensive procedure. The prepared nanocatalyst was considered as a robust and clean nano-reactor catalyst for the Suzuki and Heck C-C Cross-Coupling reactions in water as the green condition. This eco-friendly heterogeneous catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), X-Ray Diffractometer (XRD), energy-dispersive X-ray spectroscopy (EDS), inductively coupled plasma atomic emission spectroscopy (ICP), X-ray mapping, BET, thermogravimetric analysis (TGA), vibrating sample magnetometer (VSM), scanning electron microscopy (SEM) and Transmission electron microscopy (TEM) techniques. The use of a green medium, easy separation and workup, excellent reusability of the nanocatalyst and short reaction time are some outstanding advantages of this method.
- Ashraf, Muhammad Aqeel,Liu, Zhenling,Zhang, Dangquan,Alimoradi, Ashkan
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- Extended architectures constructed of thiourea-modified SBA-15 nanoreactor: A versatile new support for the fabrication of palladium pre-catalyst
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We designed and synthesized a novel catalyst consisting of ordered mesoporous silica (SBA-15) functionalized with bis(thiourea) (BTU) linker. The regular and unique pore channels of BTU-SBA-15 ensure proper control of the size and homogeneous distribution of palladium nanoparticles. The physiochemical properties of the hybrid Pd?BTU-SBA-15 pre-catalyst were investigated using various techniques. The proposed catalyst is found to be very active, reusable, stable and scalable, and has excellent reactivity and selectivity for Suzuki and Heck coupling reactions under very mild and sustainable reaction conditions.
- Alamgholiloo, Hassan,Noroozi Pesyan, Nader,Rostamnia, Sadegh
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- Facile fabrication of magnetically separable palladium nanoparticles supported on modified kaolin as a highly active heterogeneous catalyst for Suzuki coupling reactions
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In this study, Fe3O4 loaded Schiff base modified kaolin was prepared as a new support and palladium nanoparticles were anchored on it without any additional reducing agent (Pd NPs&at;Kao/Fe3O4/Pyr). Characterization studies demonstrated that Pd NPs&at;Kao/Fe3O4/Pyr was successfully designed and the size of particles was about 25 nm. Pd NPs&at;Kao/Fe3O4/Pyr was then utilized as catalyst in the preparation of biaryl compounds via Suzuki cross coupling reactions. Catalytic tests showed that Pd NPs&at;Kao/Fe3O4/Pyr acted as a highly active heterogeneous nanocatalyst in the coupling reaction of aryl iodides, bromides and chlorides containing different functional groups. Moreover, it was found that Pd NPs&at;Kao/Fe3O4/Pyr was successfully used in consecutive recycling tests and gave an 89percent yield even after ten runs. In addition to the high catalytic behavior and reusability, Pd NPs&at;Kao/Fe3O4/Pyr have some advantages such as i) capability of application for various halides containing different functional groups, ii) ease of purification of final product and iii) simple work-up.
- Baran, Talat,Nasrollahzadeh, Mahmoud
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- Synthesis, characterization, crystal structure and catalytic activity of amido azo palladium(II) complex
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Abstract: The newly designed tridentate ligand, 2-((2-aminophenyl)diazenyl)-N-benzylaniline, 1 has been synthesized by the reaction between 2,2′-diaminoazobenzene and benzyl chloride in presence of K2CO3. This ligand was reacted with Na2[PdCl4] in methanol to give the new Pd(II) complex?2. Both the ligand and complex were characterized by usual spectroscopic techniques. Furthermore, the solid-state structure of complex 2 was determined using single crystal X-ray diffraction analysis. It revealed that the ligand binds with Pd(II) in dianionic tridentate (N,N,N) fashion offering distorted square planar geometry where fourth position is occupied by one phosphine ligand. The performance of the Pd(II) phosphine complex as catalyst was evaluated in the homogenous Suzuki and Heck reactions under mild conditions in presence of air and moisture. The Pd(II) complex showed good catalytic activities for the coupling of several aryl halides (iodides and bromides) with phenyl boronic acid and styrene providing excellent yields. After catalytic reactions, the catalyst has been recovered by simple chromatographic separation and reused for next reaction and its activity checked up to three cycles without sufficient loss. Graphic abstract: The newly designed tridentate ligand, 2-((2-aminophenyl)diazenyl)-N-benzylaniline and its corresponding palladium(II) complex were synthesized and structurally characterized. The neutral palladium(II) amido complex with phosphine as ancillary ligand was formed through two amino proton elimination from ligand precursor. The newly synthesized Palladium(II) complex acts as potential catalyst toward C–C bond formation for a variety of substrate under mild conditions in presence of air and moisture.[Figure not available: see fulltext.].
- Pratihar, Jahar Lal,Mandal, Paritosh,Mal, Dasarath,Lin, Chia-Her
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p. 553 - 559
(2020/06/22)
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- Pd nanoparticles supported on Fe3O4@SiO2-Schiff base as an efficient magnetically recoverable nanocatalyst for Suzuki–Miyaura coupling reaction
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Abstract: In this work, Pd nanoparticles (Pd-NPs) were decorated on modified magnetic nanoparticles (MNPs) and used as an efficient and recyclable catalyst for the Suzuki cross-coupling reaction of aryl halides with phenylboronic acid (PhB(OH)2) in a green solvent. The prepared nanocomposite was characterized by field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, Fourier transforms infrared spectroscopy, X-ray powder diffraction, thermogravimetric analysis/differential thermal analysis, and vibrating sample magnetometry. All analyses confirmed the successful modification of MNPs and immobilization of Pd on modified MNPs. This catalyst exhibited superior catalytic activity and stability in the suzuki cross-coupling reaction of PhB(OH)2 and aryl halide derivatives. This protocol includes some advantages, such as magnetically reusability of the catalyst, mild experimental conditions, green solvent, excellent yields of the product (52–98percent), and short reaction times (4–33?min). The catalyst could be reused for six successive runs without any significant loss of its efficiency. Graphic abstract: [Figure not available: see fulltext.]
- Amirmahani, Najmeh,Mahmoodi, Nosrat O.,Malakootian, Mohammad,Pardakhty, Abbas,Seyedi, Neda
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p. 4595 - 4609
(2020/08/05)
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- Method for synthesizing biphenyl compound by taking suaeda salsa extract liquor as solvent
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The invention discloses a method for synthesizing a biphenyl compound by using suaeda salsa extract as a solvent in the technical field of organic chemical synthesis, which comprises the following steps: roasting suaeda salsa in a muffle furnace to obtain ash, dissolving the ash in distilled water, refluxing, cooling the solution, and filtering to obtain a faint yellow solution which is the suaedasalsa extract liquor; sequentially adding 1mmol of aryl halide, 1.1mmol of arylboronic acid, 0.001mmol to 0.01mmol of a catalyst and 4ml of the suaeda salsa extract liquor into a round-bottom flask,stirring at 100 DEG C to react for 2 hours, cooling the reactant to room temperature, filtering, mixing the obtained filter residue with a palladium catalyst to obtain a mixture; and dissolving the mixture in ethyl acetate, filtering to remove the palladium catalyst, and drying the filtrate by distillation to obtain the biphenyl compound. According to the scheme, a phosphine ligand, alkali and anadditive do not need to be added, a Suzuki reaction system with biomass extract as a reaction medium is adopted, and a green, simple, convenient and efficient method is provided for synthesizing biphenyl compounds.
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Paragraph 0023-0024
(2020/06/30)
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- Preparation and characterization of Cu supported on 2-(1H-benzo[d]imidazol-2-yl)aniline-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for Ullmann and Suzuki cross-coupling reactions
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Copper supported on 2-(1H-benzo[d]imidazol-2-yl)aniline (BIA)-functionalized Fe3O4 nanoparticles (Cu-BIA-Si-Fe3O4) as a novel magnetic catalyst was designed and used for the synthesis of new products via Ullmann and Suzuki cross-coupling reactions. The Ullmann reaction was performed by mixing arylboronic acid with aniline derivatives in dimethylsulfoxide solvent. Also, diaryls were synthesized via Suzuki C–C reactions between aryl halides and phenylboronic acid in the same solvent. The prepared materials and catalyst were characterized with various analytical techniques. The Cu-BIA-Si-Fe3O4 catalyst demonstrated catalytic efficiency with good to excellent yields for both types of reactions in comparison with commercial palladium catalysts. Also, the catalyst could be recovered by a simple filtration and retained its activity even after several cycles.
- Danqing, Liang,Ming, Jin,Li, Li,Mohammadnia, Majid
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- A two-dimensional amide-linked covalent organic framework anchored Pd catalyst for Suzuki-Miyaura coupling reaction in the aqueous phase at room temperature
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A two-dimensional amide-linked covalent organic frameworks (2D-COFs) supported Pd catalysis system was synthesized. Fourier transformed Infrared (FTIR), X-ray diffraction (XRD) and X-ray photoelectron spectroscopy (XPS) are used to characterize the prepared catalyst. Electron microscopes (SEM and TEM) are employed to know the morphologies of the synthesized catalysts. The catalyst is an efficient heterogeneous catalyst for Suzuki-Miyaura coupling reaction, exhibits high catalytic activity for various aryl halides and aryl boronic acids in aqueous media at room temperature. More importantly, the catalyst with high stability could be easily recycled for at least nine runs without decrease of the catalytic activity.
- Wu, Shang,Ding, Ning,Jiang, Pengwei,Wu, Lan,Feng, Qiaoliang,Zhao, Lianbiao,Wang, Yanbin,Su, Qiong,Zhang, Hong,Yang, Quanlu
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supporting information
(2020/12/02)
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- Method for synthesizing nitrobiphenyl
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The invention relates to a method for synthesizing nitrobiphenyl. The nitrophenylamine which is low in price and benzene are mixed in a solvent which contains halogenated organic acid, halogenated metal salt and nitrite and react, and then the nitrobiphenyl is obtained by aftertreatment. The raw materials are simple and are easily obtained, and are low in cost. Meanwhile, reaction conditions are mild, aftertreatment is simple, and industrialization is facilitated.
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Paragraph 0056; 0057
(2020/07/24)
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- Sulphonic acid functionalized porphyrin anchored with a: Meso -substituted triazolium ionic liquid moiety: A heterogeneous photo-catalyst for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation
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We report an easy process to synthesize sulphonic acid functionalized porphyrin, anchored with a meso-substituted triazolium ionic liquid moiety (SAFPTILM) for metal/base free C-C cross-coupling and C-N/C-H activation using aryl chloride under visible light irradiation. The acid strength has been measured based on the Hammett indicator. The SAFPTILM photocatalyst comprising 18 π-conjugated electronic systems with the chromophore substituents in the meso-position can provide rapid electronic conducting channels during photocatalysis under the irradiation of visible light. It was found that SAFPTILM is an efficient photocatalyst for the Heck, Sonogashira, Buchwald, Ullmann/Fittig coupling and C-H activation of phenols with different aryl chlorides in the absence of a base/noble metal, using 5 W LED (yellow) light under ambient conditions. The photocatalyst with low band gap (1.55 eV) comprising conjugation, favors coupling reaction of unactivated aryl chlorides, by easy excitation of electrons and transfer to the conjugated benzimidazolium based phenylenediamine support delaying the recombination of photoinduced electron-hole pairs.
- Bhansali, Karan,Raut, Subodh,Barange, Shital,Bhagat, Pundlik
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p. 19690 - 19712
(2020/12/04)
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- A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls
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A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.
- Hu, Rui,Li, Xinmin,Ren, Changyue,Yuan, Zeli,Zhang, Hang,Zhang, Tingting
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supporting information
p. 4748 - 4753
(2020/08/17)
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- Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects
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Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.
- Antenucci, Achille,Barbero, Margherita,Dughera, Stefano,Ghigo, Giovanni
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- Supramolecular photocatalyst of Palladium (II) Encapsulated within Dendrimer on TiO2 nanoparticles for Photo-induced Suzuki-Miyaura and Sonogashira Cross-Coupling reactions
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In this study, synthesis, characterization and catalytic performance of a novel supramolecular photocatalytic system including palladium (II) encapsulated within amine-terminated poly (triazine-triamine) dendrimer modified TiO2 nanoparticles (Pd (II) [PTATAD] @ TiO2) is presented. The obtained nanodendritic catalyst was characterized by FT-IR, ICP-AES, XPS, EDS, TEM, TGA and UV-DRS. The as-prepared nanodendritic catalyst was shown to be highly active, selective, and recyclable for the Suzuki–Miyaura and Sonogashira cross-coupling of a wide range of aryl halides including electron-rich and electron-poor and even aryl chlorides, affording the corresponding biaryl compounds in good to excellent yields under visible light irradiation. This study shows that visible light irradiation can drive the cross-coupling reactions on the Pd (II) [PTATAD] @ TiO2 under mild reaction conditions (27–30?°C) and no additional additives such as cocatalysts or phosphine ligands. So, we propose that the improved photoactivity predominantly benefits from the synergistic effects of Pd (II) amine-terminated poly (triazine-triamine) dendrimer on TiO2 nanoparticles that cause efficient separation and photogenerated electron–hole pairs and photoredox capability of nanocatalyst which all of these advantages due to the tuning of band gap of catalyst in the visible light region.
- Eskandari, Ameneh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Salimi, Mehri
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- Band Gap Modification of TiO2 Nanoparticles by Ascorbic Acid-Stabilized Pd Nanoparticles for Photocatalytic Suzuki–Miyaura and Ullmann Coupling Reactions
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In this study, synthesis, characterization and photocatalytic performance of surface-modified TiO2 nanoparticles with ascorbic acid-stabilized Pd nanoparticles are presented. The structure, composition and morphology of as-prepared nanophotocatalyst were characterized by UV-DRS, FT-IR, ICP-AES, TEM and XPS analysis. Ascorbic acid-stabilized Pd nanoparticles induced visible light driven photocatalytic property on the surface of TiO2 which are otherwise insensitive to visible light owing to the wide band gap. The catalytic system worked well for the Suzuki–Miyaura cross-coupling and Ullmann homocoupling under compact fluorescent light as a visible source with significant activity, selectivity and recyclability. Good to excellent yields of biaryl products were obtained for various aryl halides having different electronic demands and even aryl chlorides. Our results proposed that the improved photoactivity predominantly benefits from the synergistic effects of ascorbic acid-stabilized Pd nanoparticles on TiO2 nanoparticles that cause efficient separation and photoexcited charge carriers and photoredox capability of nanocatalyst. Thus, tuning of band gap of TiO2 making a visible light sensitive photocatalyst, demonstrates a significant advancement in the photocatalytic Suzuki–Miyaura and Ullmann coupling reactions. Graphical Abstract: [Figure not available: see fulltext.].
- Feizpour, Fahimeh,Jafarpour, Maasoumeh,Rezaeifard, Abdolreza
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- Pd nanoparticles immobilized on the magnetic silica–chitosan nanocomposite (NiFe2O4@SiO2@CS-Pd NPs) promoted the biaryl synthesis
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NiFe2O4 nanoparticles have been prepared by co-precipitation procedure and coated with SiO2 following the St?ber process. Then, chitosan was covalently connected with silica to provide an excellent stabilizer and biosupport for the immobilization of Pd nanoparticles. This magnetic bionanocatalyst was characterized by Fourier transform infrared spectroscopy, field-emission scanning electron microscope, transmission electron microscope, energy-dispersive X-ray, X-ray powder detection, vibrating sample magnetometer, inductively coupled plasma atomic emission spectroscopy techniques and CHN analysis. The NiFe2O4@SiO2@CS-Pd NPs exhibited high activity for the Suzuki coupling reactions of various aryl halides with arylboronic acids. Moreover, this catalyst could be recovered magnetically and recycled for nine times without significant loss of its activity.
- Rafiee, Fatemeh,Hosseini, S. Azam
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p. 1993 - 2001
(2019/07/04)
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- Pd nanoparticles stabilized on the Schiff base-modified boehmite: Catalytic role in Suzuki coupling reaction and reduction of nitroarenes
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Palladium nanoparticles (Pd NPs) were decorated on Schiff base-modified boehmite (Sch-boehmite) particles via a simple method without deploying any additional reducing agents and their structure was confirmed by different characterization methods. The ensuing Pd NPs?Sch-boehmite was evaluated as a retrievable catalyst for multiple cycles in Suzuki cross-coupling reactions with extensive substrate tolerance to produce biaryls in high yields within 6 min, and the reduction of 2-nitroaniline (2-NA) and 4-nitrophenol (4-NP) at room temperature in 3–4 min, respectively. Moreover, Pd NPs?Sch-boehmite catalyst could be conveniently recovered and reused multiple times.
- Baran, Nuray Y?lmaz,Baran, Talat,Nasrollahzadeh, Mahmoud,Varma, Rajender S.
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- Palladium nanoparticles decorated on a novel polyazomethine as a highly productive and recyclable catalyst for Suzuki coupling reactions and 4-nitrophenol reduction
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This report displays the procedure in preparation of fast, highly productive, reusable, and easily retrievable Pd nanoparticles (NPs) as a heterogeneous catalyst (Pd NPs?P(3-MPAP)) immobilized on a novel polyazomethine with phenol group, Poly(3-methyl-4-((pyridin-2-ylmethylene)amino)phenol) (P(3-MPAP)), and the investigation of its catalytic efficiency in fabrication of several biaryl compounds by Suzuki coupling reactions and reduction of 4-nitrophenol to 4-aminophenol. The structures of the synthesized monomer, polymer support material and nanocatalyst were identified by UV–Vis, FT-IR, 1H NMR, TGA, XRD, SEM and EDS methods. The catalytic activity of Pd NPs?P(3-MPAP) catalyst in the synthesis of various biaryls by Suzuki coupling reactions was explored using microwave irradiation, which is rapid, easy, solventless and environmentally friendly method. The nanocatalyst presented outstanding advantageous methodology containing easy work-up with high reaction yield (99%) at very short reaction time (5 min) in solventless media using very low catalyst loading (0.007 mol%) in the synthesis of biaryls. Additionally, the harmful 4-nitrophenol was completely reduced to industrially useful 4-aminophenol in the presence of Pd NPs?P(3-MPAP) with low catalyst amount (1 mg), at very short reaction time (60s) without any toxic solvent (in water) at room temperature. Additionally, reproducibility test results for both catalytic reactions show that the highly productive nanocatalyst was easily retrievable and reusable for six and five sequential cycles, respectively, for Suzuki coupling reactions and reduction of 4-NP without any notable loss in its catalytic activity.
- Y?lmaz Baran
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- Production and Application of Highly Efficient and Reusable Palladium Nanocatalyst Decorated on the Magnetically Retrievable Chitosan/Activated Carbon Composite Microcapsules
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Abstract: This study reports (i) the production of magnetically retrievable microcapsules as immobilizing agents, which are composed of chitosan/activated carbon composite (CS-AC/Fe3O4), (ii) the green synthesis of highly stable palladium nanoparticles on CS-AC/Fe3O4 without using any toxic reducing agents (Pd NPs@CS-AC/Fe3O4), (iii) the investigation of catalytic behavior of Pd NPs@CS-AC/Fe3O4 in Suzuki–Miyaura reactions of different aryl iodides, bromides, and chlorides, and (iv) the examination of recoverability and reusability of Pd NPs@CS-AC/Fe3O4. The characterization of Pd NPs@CS-AC/Fe3O4 was performed by FT-IR, TG/DTG, XRD, SEM, and EDS analyses. It was found that the average sizes of palladium nanoparticles were changed in the range of 31–48?nm. The catalytic tests revealed that Pd NPs@CS-AC/Fe3O4 was a very effective catalyst against synthesis of various biaryl compounds via Suzuki–Miyaura reactions, by giving high reaction yields under mild reaction conditions. Furthermore, it was found that Pd NPs@CS-AC/Fe3O4 was a highly retrievable and practical nanocatalyst due to its reusable nature. Pd NPs@CS-AC/Fe3O4 gave 95% of yield after ten successive cycles. These results show that Pd NPs@CS-AC/Fe3O4 is a superb catalyst and it can be applied in different catalytic systems or industrial applications due to the fact that it offers notable advantages such as high catalytic performance, reusability, stability, excellent functional group tolerance, wide substrate scope, and simple separation. Graphical Abstract: [Figure not available: see fulltext.].
- Baran, Talat
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- Facile synthesis of palladium nanoparticles immobilized on magnetic biodegradable microcapsules used as effective and recyclable catalyst in Suzuki-Miyaura reaction and p-nitrophenol reduction
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This study reports (i) preparation and characterization of palladium nanoparticles (Pd NPs) stabilized on magnetically separable chitosan/agar microcapsules (Pd NPs@Fe3O4/CS-AG microcapsules) and (ii) investigation of catalytic behaviors of the prepared nanoparticles in Suzuki-Miyaura C-C cross-coupling reactions and reduction of p-nitrophenol (p-NP). Fourier transforms infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), X-ray diffraction (XRD), elemental mapping, inductively coupled plasma-optical emission spectrometry (ICP-OES) and thermogravimetry/derivative thermogravimetry (TG/DTG) techniques were used for analyzing the Pd NPs@Fe3O4/CS-AG microcapsules. Characterization studies showed that Pd NPs@Fe3O4/CS-AG microcapsules were successfully synthesized and the size of the particles was in the range of 28–39 nm. Pd NPs@Fe3O4/CS-AG microcapsules displayed highly effective catalytic performance in the conversion of various aryl halides into the corresponding biaryl derivatives by Suzuki-Miyaura reaction under solvent-free conditions in 5 min. Pd NPs@Fe3O4/CS-AG microcapsules were also successfully employed in p-NP reduction to p-aminophenol (p-AP) in water at room temperature in 180 s. Moreover, reproducibility studies showed that Pd NPs@Fe3O4/CS-AG microcapsules were highly efficient and could be used many times in both catalytic reactions due to their magnetically separable nature. According to the results of this work, Pd NPs@Fe3O4/CS-AG microcapsules are highly efficient, economical, practical and environmentally superb catalysts for Suzuki-Miyaura reaction and p-NP reduction.
- Baran, Talat,Nasrollahzadeh, Mahmoud
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- Tetradentate amido azo Schiff base Cu(II), Ni(II) and Pd(II) complexes: Synthesis, characterization, spectral properties, and applications to catalysis in C–C coupling and oxidation reaction
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New Schiff base ligands (H2L1 & H2L2) were synthesized by the reaction of salicylaldehyde with (2-((2-aminophenyl)diazenyl)-N-alkylaniline), and were used for the preparation of complexes with Cu(II), Ni(II) and Pd(II) metal ions. The structural features of the synthesized compounds were examined by UV–Vis, IR and 1H NMR spectroscopy. The crystal structures of Schiff base (H2L1) and two metal complexes Cu(L1) and Ni(L2) were determined by single crystal X-ray diffraction. The studies revealed that the synthesized Schiff bases existed as tetradentate (N,N,N,O) ligands and bonded to the metal ions through the donor atoms of the amido nitrogen, azo nitrogen, azomethine nitrogen and phenolic oxygen atoms. The redox property of Cu(L1) and Ni(L1) and emission behavior of ligand H2L1 and complexes Cu(L1) and Ni(L1) were examined. The complex Cu(L1) shows excellent catalytic activity towards oxidation of benzyl alcohol to benzyldehyde (under solvent-free condition) using H2O2 as the oxidant. Complex Pd(L1) acts as highly efficient catalyst in the Suzuki–Miyaura cross-coupling reaction of various aryl halides with phenyl boronic acid to produce the corresponding biaryls with high yields under mild reaction conditions. Both the catalysts Cu(L1) and Pd(L1) were easily recovered by simple chromatographic separation and reused for next catalytic cycle.
- Pratihar, Jahar Lal,Mandal, Paritosh,Lai, Chung Kung,Chattopadhyay, Surajit
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p. 317 - 324
(2019/02/06)
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- Journey on Greener Pathways via Synthesis of Pd/KB Polymeric Nanocomposite as a Recoverable Catalyst for the Ligand-Free Oxidative Hydroxylation of Phenylboronic Acid and Suzuki–Miyaura Coupling Reaction in Green Solvents
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This paper reports a new and straightforward technique for the preparation of catalytically active palladium nanoparticle (Pd NPs) supported on the polymer surface derived from virgin polythene (Kaldnes Bio media filter) (Pd/KB nanocomposite). The morphology, structure and composition of Pd/KB nanocomposite were characterized by SEM, TEM, XRD, EDX and UV–Vis spectroscopy. The as-prepared catalyst presented excellent catalytic activity for the ligand-free oxidative hydroxylation of phenylboronic acid and Suzuki–Miyaura coupling reaction in water and ethanol as green solvents. In addition, the catalyst could be easily separated from the reaction mixture and reused four times with no loss of activity. The advantages of this eco-friendly protocol are using the cheap, clean, and nontoxic precursors, simple reaction setup, high yield of products and elimination of ligand and homogeneous catalysts. Graphical Abstract: [Figure not available: see fulltext.]
- Feizi Mohazzab, Bahareh,Jaleh, Babak,Nasrollahzadeh, Mahmoud,Issaabadi, Zahra
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p. 169 - 179
(2018/10/31)
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- Nickel-metalated porous organic polymer for Suzuki-Miyaura cross-coupling reaction
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A new Ni(ii)-α-diimine-based porous organic polymer, namely Ni(ii)-α-diimine-POP, was constructed in high yield via the Sonogashira coupling reaction between the metallo-building block of Ni(ii)-α-diimine and 1,3,5-triethynylbenzene. Besides the high thermal and chemical stability, the obtained Ni(ii)-α-diimine-POP can be a highly active reusable heterogeneous catalyst to promote the Suzuki-Miyaura coupling reaction. The obtained results indicate that the Ni(ii)-α-diimine-POP herein is a promising sustainable alternative to the Pd-based catalysts for catalysing the C-C formation in a heterogeneous way.
- Dong, Ying,Jv, Jing-Jing,Li, Yue,Li, Wen-Han,Chen, Yun-Qi,Sun, Qian,Ma, Jian-Ping,Dong, Yu-Bin
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p. 20266 - 20272
(2019/07/10)
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- A palladium-carbon-connected organometallic framework and its catalytic application
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Herein, we report an organometallic framework (OMF) generated from a divergent tridentate arylisocyanide ligand and PdI2 under solvothermal conditions. The obtained Pd-C bond-connected two-dimensional Pd-OMF was crystalline and porous. Moreover, it could be a highly active catalyst to promote the Suzuki-Miyaura cross-coupling reaction in a heterogeneous manner.
- Dong, Ying,Jv, Jing-Jing,Wu, Xiao-Wei,Kan, Jing-Lan,Lin, Ting,Dong, Yu-Bin
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supporting information
p. 14414 - 14417
(2019/12/09)
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- Pd-Au-Y as Efficient Catalyst for C-C Coupling Reactions, Benzylic C-H Bond Activation, and Oxidation of Ethanol for Synthesis of Cinnamaldehydes
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Pd-Au nanoalloy supported on zeolite-Y (Pd-Au-Y) matrix was found to be an effective catalyst for C-Cl bond activation and oxidative coupling of 2-naphthol, leading to the formation of various biaryl products and 1,1′-bi-2-naphthol, BINOL. The same catalyst was also highly efficient for selective oxidation of benzylic alcohols to benzaldehydes. Cinnamaldehydes were obtained directly from benzaldehydes by aldol condensation with acetaldehyde generated in situ by partial oxidation of ethanol in the presence of Pd-Au-Y catalyst at 120 °C under basic condition. The biaryl products were also obtained directly from benzylic alcohols in a one-pot system by reacting with phenylboronic acid. The formation of biaryls from benzylic alcohols was believed to occur via one-pot benzylic C-H and C-Cl bond activation. A high % yield of biaryls, BINOL, aldehydes, and cinnamaldehydes was obtained by performing different reactions using the single Pd-Au-Y catalyst. The strong interaction of chloro-benzylic alcohol was predominantly located at active gold species. X-ray photoelectron and diffuse reflectance spectroscopic studies revealed the strong interaction between Pd and Au particles. Electrochemical studies provided proper evidence for the individual role of the nanoparticles (NPs) in one-pot synthesis of biaryls from benzylic alcohols.
- Sharma, Mukesh,Das, Biraj,Baruah, Manash J.,Biswas, Subir,Roy, Subhasish,Hazarika, Anil,Bhargava, Suresh K.,Bania, Kusum K.
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p. 5860 - 5875
(2019/06/17)
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- Alpha-diimine nickel metal organic ligand, porous organic polymer and application of porous organic polymer
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The disclosure provides an alpha-diimine nickel metal organic ligand, a porous organic polymer and application of the porous organic polymer. The porous organic polymer has a chemical structural formula as shown in the description. The porous organic polymer can be applied to preparation of a catalyst for catalyzing a Suzuki coupling reaction, and the catalyst has high catalytic activity, low cost, low usage amount and repeated use.
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Paragraph 0092-0093; 0106-0110
(2019/10/01)
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- Tridentate carbene, and preparation method and application thereof
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The invention provides a tridentate carbene, and a preparation method and an application thereof. The tridentate carbene has a structure represented by formula [1]; and in the formula [1], R1 and R2 are independently selected from substituted or unsubstituted C1-10 chain alkyl groups, C3-10 cycloalkyl groups, C2-10 alkenyl groups, C2-10 alkynyl groups and aryl groups. The tridentate carbene has astrong catalytic performance, and can be used in various reactions as a catalyst, and the preparation method is simple and easy.
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Paragraph 0129-0133; 0146-0150
(2019/10/01)
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