- Effects of P-glycoprotein on the transport of DL0410, a potential multifunctional anti-Alzheimer agent
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In our study, we attempted to investigate the influences of P-glycoprotein (P-gp) on DL0410, a novel synthetic molecule for Alzheimer’s disease (AD) treatment, for intestinal absorption and blood-brain barrier permeability in vitro and related binding mechanisms in silico. Caco-2, MDCK, and MDCK-MDR1 cells were utilized for transport studies, and homology modelling of human P-gp was built for further docking study to uncover the binding mode of DL0410. The results showed that the apparent permeability (Papp) value of DL0410 was approximately 1 × 10?6 cm/s, indicating the low permeability of DL0410. With the presence of verapamil, the directional transport of DL0410 disappeared in Caco-2 and MDCK-MDR1 cells, suggesting that DL0410 should be a substrate of P-gp, which was also confirmed by P-gp ATPase assay. In addition, DL0410 could competitively inhibit the transport of Rho123, a P-gp known substrate. According to molecular docking, we also found that DL0410 could bind to the drug binding pocket (DBP), but not the nucleotide binding domain (NBD). In conclusion, DL0410 was a substrate as well as a competitive inhibitor of P-gp, and P-gp had a remarkable impact on the intestine and brain permeability of DL0410, which is of significance for drug research and development.
- Pang, Xiaocong,Wang, Lin,Kang, De,Zhao, Ying,Wu, Song,Liu, Ai-Lin,Du, Guan-Hua
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Read Online
- Effects of length and number of aromatic rings in carboxylic acid ligands on structure and optical properties of lead(II) coordination polymers
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To systematically examine the effects of the length and number of aromatic rings in carboxylic acid ligands on the structure and properties of lead(II) coordination polymers, terephthalic acid (L1) and 4,4-biphenyl dicarboxylic acid (L2) as primary ligands and 1-(dimethylamino)propan-2-ol (L3) as ancillary ligand were used for preparation of two new lead(II) coordination polymers: [Pb2L2 1L3(DMF)]n (1) and [PbL2L3]n (2). Single-crystal X-ray diffraction analysis was used to determine the crystal structure of the prepared compounds. The results showed that the length of the π-conjugation system of the aromatic carboxylic acid ligands was a primary factor controlling the structure of the coordination compounds. Connecting Pb(II) atoms using ligands L1 and L3 led to formation of compound 1 with two-dimensional network structure, while use of ligands L3 and L2 resulted in formation of compound 2 with zigzag one-dimensional (1D) polymeric network structure. Study of the thermal behavior of the prepared compounds revealed that the structure and type of the ligands in the coordination compounds affected their thermal stability. Investigation of the optical properties of the compounds demonstrated that changing the length of the π-conjugation system of the aromatic carboxylic acid ligands in the structure of the coordination compounds can be used to tune their photophysical properties.
- Hashemzadeh, Alireza,Amini, Mostafa M.,Najafi, Ezzatollah,Khavasi, Hamid Reza
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- A series of triple-stranded lanthanide(III) helicates: Syntheses, structures and single molecular magnets
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Bis-β-diketones have been proven to be effective for the construction of multiple-stranded helicates, where there commonly are two distinct Ln3+centers with subtle geometric difference. In this study, a series of triple-stranded helicates [Ln2(BTB)3(DME)2]·C6H14have been prepared with the ligand H2BTB and trivalent metallic ions, respectively [Ln?=?La (1), Ce (2), Pr (3), Eu (4), Dy (5), Ho (6) and Yb (7), H2BTB?=?4,4′-bis(4,4,4-trifluoro-1,3-dioxobutyl)biphenyl and DME?=?dimethoxyethane]. All products have been fully characterized by IR spectroscopy, elemental analysis, thermogravimetric analysis, and single-crystal X-ray diffraction analyses. Structural analysis reveals that 1–7 are isostructurally crystallized in the orthorhombic space group of Pna21and each Ln3+ion is ligated to six O atoms of three BTB ligands and two O atoms of one DME molecule. Interestingly, DME molecule as a chelator to the Ln3+centers has played a unique role in the crystallization of the triple-stranded helicate 1–7. Magnetic measurement shows that 5 displays significant single-molecule magnetic property, exhibiting magnetic slow relaxation. And the large separation between Dy3+ions in the same helicates leads to two distinct magnetic relaxation processes.
- Gao, Xingrui,Li, Hongfeng,Chen, Peng,Sun, Wenbin,Yan, Pengfei
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- An imidazolium ionic liquid having covalently attached an oxime carbapalladacycle complex as ionophilic heterogeneous catalysts for the Heck and Suzuki-Miyaura cross-coupling
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An oxime carbapalladacycle, analogous to that used as catalyst in homogeneous phase, has been derivatized to increase its ionophilicity by introducing an imidazolium group covalently attached through a chain at the complex. The resulting complex is soluble in 1-butyl-3-methylimidazolium ionic liquid (bmimPF6) and not extractable by ether. The catalytic activity of this palladium complex in bmimPF6 is, however, unsatisfactory and only increases marginally in bmimPF6/supercritical CO2. This limitation has been overcome by supporting this imidazolium palladium complex on high surface area Al/MCM-41 aluminosilicate, whereby a solid active catalyst for the Suzuki cross-coupling has been obtained. Reusability and stability over reuse for this Al/MCM-41-supported catalyst have been studied. Graphical abstract.
- Corma, Avelino,García, Hermenegildo,Leyva, Antonio
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- Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone
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A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w
- Xia, Hongyu,Wang, Ganghu,Zhao, Dongbo,Zhu, Chunyin
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supporting information
p. 922 - 929
(2022/02/10)
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- Porphyrin n-pincer pd(Ii)-complexes in water: A base-free and nature-inspired protocol for the oxidative self-coupling of potassium aryltrifluoroborates in open-air
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Metalloporphyrins (and porphyrins) are well known as pigments of life in nature, since representatives of this group include chlorophylls (Mg-porphyrins) and heme (Fe-porphyrins). Hence, the construction of chemistry based on these substances can be based on the imitation of biological systems. Inspired by nature, in this article we present the preparation of five different porphyrin, meso-tetraphenylporphyrin (TPP), meso-tetra(p-anisyl)porphyrin (TpAP), tetra-sodium meso-tetra(p-sulfonatophenyl)porphyrin (TSTpSPP), meso-tetra(m-hydroxyphenyl)porphyrin (TmHPP), and meso-tetra(m-carboxyphenyl)porphyrin (TmCPP) as well as their N-pincer Pd(II)-complexes such as Pd(II)-meso-tetraphenylporphyrin (PdTPP), Pd(II)-meso-tetra(p-anisyl)porphyrin (PdTpAP), Pd(II)-tetrasodium meso-tetra(p-sulfonatophenyl)porphyrin (PdTSTpSPP), Pd(II)-meso-tetra(m-hydroxyphenyl)porphyrin (PdTmHPP), and Pd(II)-meso-tetra(m-carboxyphenyl)porphyrin (PdTmCPP). These porphyrin N-pincer Pd(II)-complexes were studied and found to be effective in the base-free self-coupling reactions of potassium aryltrifluoroborates (PATFBs) in water at ambient conditions. The catalysts and the products (symmetrical biaryls) were characterized using their spectral data. The high yields of the biaryls, the bio-mimicking conditions, good substrate feasibility, evading the use of base, easy preparation and handling of catalysts, and the application of aqueous media, all make this protocol very attractive from a sustainability and cost-effective standpoint.
- Hanafiah, Marlia M.,Lakkaboyana, Sivarama Krishna,Lakshmidevi, Jangam,Marella, Ravi Kumar,Naidu, Bandameeda Ramesh,Prasad, Sana Siva,Venkateswarlu, Katta
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- Ultrafine and Highly Dispersed Pd/SiO2 for Suzuki?Miyaura Cross-coupling Reactions
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Abstract: Construction of heterogeneous Pd/SiO2 catalyst via the pollution-free strategy marked strong electrostatic adsorption has been reported for the application to Suzuki–Miyaura cross-coupling reactions. The exposed negatively charged oxygen groups, which were converted from the hydroxyl groups on the surface of silica under the alkaline atmosphere, could effectively anchor palladium species to form ultrafine Pd nanoparticles (Pd NPs) with an average particle size of 1.3?nm and high dispersion (43%). Pd/SiO2 catalyst was endowed with the excellent catalytic performance which was that the yield of the Suzuki–Miyaura reaction between bromobenzene and phenylboronic acid at 40?°C was > 99% for 30?min and the TOF was ~ 80,000?h?1. The catalyst could be easily recovered and recycled by facile procedure without a significant decrease in catalytic activity, which was able to maintain the 90% yield after repeated for 8 times. In addition, a continuous flow reaction device was designed using the Pd/SiO2 catalyst to effectively improve the production efficiency of biphenyl. Graphic Abstract: Pd/SiO2 catalyst constructed with the strategy of strong electrostatic adsorption (SEA) possesses uniformly dispersed and highly exposed Pd sites which can be easily transformed into electron-deficient Pdδ+ and strengthened stability for itself due to its strong interaction with the front surface of the carrier, and has been endowed the outstanding catalytic performance for Suzuki?Miyaura cross-coupling reaction. [Figure not available: see fulltext.]
- Fan, Xizheng,Yang, Jingyi,Pang, Qingqing,Liu, Zhongyi,Zhang, Panke,Yang, Jing-He
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p. 2291 - 2301
(2021/01/04)
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- Rigid Multidimensional Alkoxyamines: A Versatile Building Block Library
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Since the discovery of the “living” free-radical polymerization, alkoxyamines were widely used in nitroxide-mediated polymerization (NMP). Most of the known alkoxyamines bear just one functionality with only a few exceptions bearing two or more alkoxyamine units. Herein, we present a library of novel multidimensional alkoxyamines based on commercially available, rigid, aromatic core structures. A versatile approach allows the introduction of different sidechains which have an impact on the steric hindrance and dissociation behavior of the alkoxyamines. The reaction to the alkoxyamines was optimized by implementing a mild and reliable procedure to give all target compounds in high yields. Utilization of biphenyl, p-terphenyl, 1,3,5-triphenylbenzene, tetraphenylethylene, and tetraphenyl-methane results in linear, trigonal, square planar, and tetrahedral shaped alkoxyamines. These building blocks are useful initiators for multifold NMP leading to star-shaped polymers or as a linker for the nitroxide exchange reaction (NER), to obtain dynamic frameworks with a tunable crosslinking degree and self-healing abilities.
- Matt, Yannick,Wessely, Isabelle,Gramespacher, Lisa,Tsotsalas, Manuel,Br?se, Stefan
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supporting information
p. 239 - 245
(2020/12/17)
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- Electrochemical coupling halobenzene into biphenyl on a reusable Pd nanoparticle-coated carbon-paper electrode at ambient conditions
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Electrochemical organic synthesis (EOS) employing electrons to directly activate the reactants can readily complete the chemical conversion under mild conditions. Here, it presented an efficient electrochemical coupling halobenzene into biphenyl on a Pd nanoparticle-coated cathode. The biphenyl product can be obtained with a yield up to 77% at 35 mA, 6 h (3.9 F mol?1). In addition, after consecutive fifth run of the coupling reaction, the yield still remained atca.40%, suggesting its considerable recyclable capacity. In addition, the preliminary kinetics studyviathe off-line gas chromatography analysis of the reaction mixture shows a two-section reaction process, including the introduction process (IP) and fast conversion process (FCP). Further, the estimated reaction kinetics constant value of 0.196 min?1for FCP suggests a more effective conversion than that obtained by the previous study. This study adopts a simple way to fabricate a low-cost and reusable Pd electrode, achieving a high-efficiency electrochemical strategy for the Ullmann-type coupling reaction at mild conditions, and holds a great promise to extend this synthesis route to other important organic synthesis.
- Wang, Chao-Nan,Lu, Yong-Heng,Liu, Yue,Liu, Jun,Yang, Yao-Yue,Zhao, Zhi-Gang
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p. 3997 - 4003
(2021/03/06)
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- Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Coupling of Two sp 2-Hybridized Organohalides
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Cross-coupling reactions are essential for the synthesis of complex organic molecules. Here, we report a nickel-catalyzed Ullmann cross-coupling of two sp 2-hybridized organohalides, featuring high cross-selectivity when the two coupling partners are used in a 1:1 ratio. The high chemoselectivity is governed by the bathocuproine ligand. Moreover, the mild reductive reaction conditions allow that a wide range of functional groups are compatible in this Ullmann cross-coupling.
- Li, Yuqiang,Yin, Guoyin
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p. 1657 - 1661
(2021/09/13)
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- Dealkenylative Ni-Catalyzed Cross-Coupling Enabled by Tetrazine and Photoexcitation
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A new and general method to functionalize the C(sp3)-C(sp2) bond of alkyl and alkene linkages has been developed, leading to the dealkenylative generation of carbon-centered radicals that can be intercepted to undergo Ni-catalyzed C(sp3)-C(sp2) cross-coupling. This one-pot protocol leverages the easily procured alkene feedstocks for organic synthesis with excellent functional group compatibility without the need for a photoredox catalyst.
- Cao, Yuhui,Che, Jinteng,Chen, Han,Chen, Si-Cong,Fang, Xianhe,Guo, Yinliang,Guo, Zhixian,Kong, Lingran,Li, Chen,Lu, Jia-Tian,Luo, Tuoping,Zhang, Nan,Zhu, Qi
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supporting information
p. 14046 - 14052
(2021/09/13)
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- Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions
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Symmetrical and unsymmetrical biaryls comprises a diverse class of biologically eloquent organic compounds. We herein report, a quick and eco-friendly protocol for the synthesis of biaryls by an oxidative (aerobic) homocoupling of arylboronic acids (ABAs) using Pd(OAc)2 in water extract of pomogranate ash (WEPA) as an efficient agro-waste(bio)-derived aqueous (basic) media. The reactions were executed at ambient aerobic conditions in the absence of external base and ligand to result symmetrical biaryls in excellent yields. The use of renewable media with an effective exploitation of waste, short reaction times, excellent yields of products, easy separation of the products, unnecessating the external base, oxidant, ligand or volatile organic solvents and ambient reaction conditions are the vital insights of the present protocol.
- Appa, Rama Moorthy,Lakshmidevi, Jangam,Naidu, Bandameeda Ramesh,Venkateswarlu, Katta
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- Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds
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A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]
- Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong
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p. 2134 - 2141
(2021/09/29)
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- MICRO-ELECTROLYSIS REACTOR FOR ULTRA FAST, OXIDANT FREE, C-C COUPLING REACTION AND SYNTHESIS OF DACLATASVIR ANALOGS THEREOF
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The present invention relates to a continuous micro-electro-flow reactor system for ultra-fast, oxidant free, C—C coupling reaction for making symmetrical biaryls and analogs thereof. This invention further relates to the said process for preparation of antiviral drug, daclatasvir of general formula I.
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Paragraph 0145-0151
(2020/12/01)
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- Exploring the coordination confinement effect of divalent palladium/zero palladium doped polyaniline-networking: As an excellent-performance nanocomposite catalyst for C-C coupling reactions
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A pre-formed catalyst Pd2+/PANI composite for C-C coupling reaction was synthesized by combining the self-stabilized dispersion polymerization method with the in-situ composite material. Experiments have confirmed that the relatively high reduced structure (75%) in the polyaniline carrier is more favorable for the coupling reaction. Raman spectroscopy, solid nuclear magnetic, and X-ray photoelectron spectroscopy were performed to characterize the structures. The pre-formed catalyst has uniform coordination of divalent palladium and nitrogen in different valence states of the carrier polyaniline, which shows a good synergistic effect in the catalytic Ullmann reaction, and greatly reduces the use of reducing agents such as hydrazine hydrate. Compared with other studies, we analyzed the catalytic reaction mechanism in detail through real-time online infrared and XPS characterization. The results show that the divalent palladium in the catalyst and the zero-valent palladium generated by the in-situ reaction synergistically promote the reaction, while the polyaniline support acts as a stabilizer and dispersant, which prevents the agglomeration of the metal particles and prolongs increased catalyst life. The prepared Pd2+/PANI composites will become the most attractive alternative to traditional organic materials due to their wide applicability, high catalytic activity, stable recycling and relatively low price. This work provides a new theoretical basis for the understanding of the essential driving force of PANI catalytic activity and the cognition of the micro mechanism of action.
- Liang, Yanping,Liu, Wanyi,Song, Manrong,Sun, Yanyan,Wang, Gang,Wu, Zhiqiang,Zhan, Haijuan
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p. 177 - 188
(2020/03/17)
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- Palladium/Sensory Component-Catalyzed Homocoupling Reactions of Aryl Halides
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A novel and efficient catalyst system was developed for homocoupling reactions of aryl halides. The catalyst system consists of Pd(OAc) 2and the peppery sensory component of tobacco leaves. This is the first time that a sensory component has been used in an organic reaction. Experiments using the catalyst system showed that the reactions proceeded smoothly under air in the absence of both an additional ligand and a reductant. Furthermore, the catalyst system can be applied to the coupling reactions of hetaryl iodides. Many functional groups (including a hydroxy group) are tolerated.
- Bai, Haixin,Bao, Fengyu,Chai, Guobi,Liu, Pengfei,Liu, Zhikai,Zhang, Haiyan,Zhang, Qidong
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supporting information
(2020/09/09)
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- Efficient Pd-catalyzed oxidative homocoupling of arylboronic acids in aqueous NaClO
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An efficient, mild and practical method was developed for the synthesis of biaryls via the Pd-catalyzed oxidative homocoupling of aromatic/heteroaromatic boronic acids in aqueous NaClO.
- Li, Min-Xin,Tang, Yan-Ling,Gao, Hui,Mao, Ze-Wei
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supporting information
(2020/03/04)
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- Copper quinolate: A simple and efficient catalytic complex for coupling reactions
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We describe an effective and novel method to prepare N-aryl imidazoles via the copper quinolate-catalyzed N-arylation of aryl halides and imidazoles. A wide range of products were obtained in moderate to excellent yields under the optimal reaction conditions. Applying standard conditions, the model reaction could be performed on a gram scale. This method also presents a new avenue to the “click” reaction of terminal alkynes, benzyl bromide, and sodium azide and to the construction of C–C bonds by homocoupling of phenylboronic acid or phenylacetylene derivatives with the aid of copper quinolate.
- Wu, Fengtian,Li, Huiqin,Xie, Jianwei
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- A Convoluted Polyvinylpyridine-Palladium Catalyst for Suzuki-Miyaura Coupling and C?H Arylation
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The development of highly active and reusable supported catalysts for Suzuki-Miyaura coupling and catalytic C?H arylation is important for fundamental and applied chemistry, with these reactions being used to produce medical compounds and functional materials. Herein, we found that a mesoporous composite made of a linear poly(4-vinylpyridine) and tetrachloropalladate acted as a dual-mode catalyst for a variety of cross-coupling reactions, with both Pd nanoparticles and a Pd complex catalyst being observed under different conditions. The polyvinylpyridine-palladium composite 1 was readily prepared via the molecular convolution of poly(4-vinylpyridine) and sodium tetrachloropalladate to provide a hardly soluble polymer-metal composite. The Suzuki-Miyaura coupling and the C?H arylation of aryl chlorides and bromides with arylboronic acids, thiophenes, furans, benzene, and anisole proceeded in the presence of 0.004 mol% (40 mol ppm) to 1 mol% Pd of 1 to afford the corresponding coupling products in high yields. Furthermore, the catalyst was reused without an appreciable loss of activity. Pharmaceutical compounds and functional materials were synthesized via the coupling reactions. N2 gas adsorption/desorption analysis indicated that the catalyst had a mesoporous nature, which played a crucial role in the catalysis. In the Suzuki-Miyaura couplings, in situ generated palladium nanoparticles in the polymer matrix were catalytically active, while a polymeric Pd(II) complex was crucial in the C?H arylations. These catalytic species were investigated via XAFS, XPS, far-infrared absorption, and Raman spectroscopies, as well as DFT calculations. (Figure presented.).
- Ohno, Aya,Sato, Takuma,Mase, Toshiaki,Uozumi, Yasuhiro,Yamada, Yoichi M. A.
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supporting information
p. 4687 - 4698
(2020/09/07)
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- Visible-Light-Enhanced Suzuki–Miyaura Reactions of Aryl Chlorides in Water with Pd NPs Supported on a Conjugated Nanoporous Polycarbazole
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The visible-light-enhanced catalytic activation of aryl chlorides for Suzuki–Miyaura cross-coupling (SMC) reactions is highly challenging because of the strength of the C?Cl bond. In this work, palladium nanoparticles (Pd NPs) were grown on a conjugated nanoporous polycarbazole (CNP), named Pd/CNP. The hybrid material Pd/CNP could catalyze the SMC reactions of aryl chlorides with arylboronic acids in water under blue LED irradiation at room temperature with high efficiency. This protocol exhibited good functional group tolerance and the catalyst could be recycled without significant loss of its catalytic activity. CNP not only provided photogenerated electrons to enrich the electron density of the Pd NPs but also generated holes for the activation of the arylboronic acids.
- Guo, Bin,Li, Hong-Xi,Zha, Cheng-Hao,Young, David James,Li, Hai-Yan,Lang, Jian-Ping
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p. 1421 - 1427
(2019/02/26)
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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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- Palladium nanoparticles immobilized on the magnetic few layer graphene support as a highly efficient catalyst for ligand free Suzuki cross coupling and homo coupling reactions
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In this study, we prepared a magnetic metal–graphene nanocomposite for the synthesis of substituted biaryls via Suzuki cross coupling and homo coupling reaction of aryl halides. The magnetic few layer graphene composite was synthesized by using one-step electrochemical exfoliation of graphite foil in aqueous iron (II) ammonium sulfate as electrolyte without using of any additive or corrosive media. Then, Fe2O3@FLG composite was used an efficient support for the immobilization and suitable dispersing of palladium nanoparticles. The obtained Fe2O3@FLG@Pd0 nanocomposite was characterized using FT-IR, SEM, TEM, EDS, XRD, VSM and ICP-AES analysis. Very low loading of this catalyst was displayed high activity in the producing substituted biaryls. It simply recovered from the reaction mixture and reused without any pre-activation in six consecutive runs with no loss of its catalytic activity or the observation of any detectable palladium leaching process.
- Rafiee, Fatemeh,Khavari, Parvaneh,Payami, Zahra,Ansari, Narges
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- Copper-catalyzed Mizoroki-Heck coupling reaction using an efficient and magnetically reusable Fe3O4@SiO2@PrNCu catalyst
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This study intends to design and prepare a new magnetic copper catalyst and its activity was assessed by carbon-carbon coupling reactions. For this purpose, 1-[3-(trimethoxysilyl) propyl] urea (TMSPU), hydrazine and CuI were used sequentially to modify Fe3O4@SiO2 core-shell magnetic nanoparticles to obtain an efficient magnetic transition metal catalyst. Various analytical techniques were used to characterize the catalyst to show that the achieved structure and its properties are well-suited for coupling reactions. Finally, Mizoroki-Heck and Ullmann coupling reactions were performed using Fe3O4@SiO2@PrNCu catalyst. The new catalyst offer simple synthetic procedure, convenient use for routine casework and low price. The Fe3O4@SiO2@PrNCu catalyst was easily separated by means of a permanent and ordinary magnet and the recovered catalyst was reused in six cycles without any significant loss of activity.
- Yavari, Issa,Mobaraki, Akbar,Hosseinzadeh, Zhila,Sakhaee, Nader
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supporting information
p. 236 - 246
(2019/07/19)
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- Desulfurization of Diaryl(heteroaryl) Sulfoxides with Benzyne
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Two benzyne-enabled desulfurization reactions have been demonstrated which convert diaryl sulfoxides and heteroaryl sulfoxides to biaryls and desulfurized heteroarenes, respectively. The reaction accessing biaryls tolerates a variety of functional groups, such as halides, pseudohalides, and carbonyls. Mechanistic studies reveal that both reactions proceed via a common assembly process but divergent disassemblies of the generated tetraaryl(heteroaryl) sulfuranes.
- Chen, De-Li,Sun, Yan,Chen, Mengyuan,Li, Xiaojin,Zhang, Lei,Huang, Xin,Bai, Yihui,Luo, Fang,Peng, Bo
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supporting information
(2019/06/13)
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- Synthesis and characterization of a new zwitterionic palladium complex as an environmentally friendly catalyst for the Heck-Mizoroki coupling reaction in GVL
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A new zwitterionic Palladium (II) complex has been synthesized by the one-pot mixing of Pd(OAc)2, 2-aminophenol and (3-formyl-4-hydroxy-5-methylbenzyl) triphenylphosphonium chloride, in refluxing ethanol. The metal complex formed was characterized by 1H NMR, 13C NMR, 31P NMR and X-ray crystallographic technique and its efficiency tested as a homogeneous pre-catalyst in Heck-Mizoroki cross coupling reaction using γ-Valerolactone (GVL) as a biomass-derived green medium. All the products were obtained in good to excellent yields.
- Bagherzadeh, Mojtaba,Mahmoudi, Hamed,Ataie, Saeed,Bahjati, Mohammad,Kia, Reza,Raithby, Paul R.,Vaccaro, Luigi
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- A green synthesis of biaryls in water catalyzed by palladium nanoparticles immobilized on N-amidinoglycine-functionalized iron oxide nanoparticles
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Fe3O4 nanoparticles were prepared by co-precipitation and coated with SiO2 following the St?ber process. N-Amidinoglycine amino acid was then covalently connected to provide an excellent ligand for the immobilization of Pd nanoparticles. The resulting material was characterized by FE-SEM, TEM, EDX, XRD, VSM and ICP-AES analysis. The Fe3O4@SiO2@N-amidinoglycine@Pd0 proved to be a highly active catalyst for the Suzuki coupling reactions of various aryl halides with substituted phenylboronic acids in water, giving the desired products in excellent yields for short reaction times. Moreover, this catalyst can be easily recovered by using an external magnet and directly reused for several times without significant loss of activity.
- Rafiee, Fatemeh,Mehdizadeh, Nasrin
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p. 295 - 300
(2018/03/23)
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- CNC pincer palladium complex supported on magnetic chitosan as highly efficient and recyclable nanocatalyst in C─C coupling reactions
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A stable and durable magnetic chitosan-supported triazine-bridged bisimidazolium pincer palladium catalyst (Fe3O4@ChC@CNC-PdII) was synthesized and characterized using various techniques. The Fe3O4@ChC@CNC-PdII complex displayed high activity in the production of substituted biaryls via the cross-coupling reactions of aryl halides with arylboronic acids. Also, this catalyst could be simply recovered from the reaction mixture and reused in 13 consecutive runs with no loss of its catalytic activity.
- Rafiee, Fatemeh,Hosseini, S. Azam
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- Palladium N-Heterocyclic Carbene Complex of Vitamin B1 Supported on Silica-Coated Fe3O4 Nanoparticles: A Green and Efficient Catalyst for C–C Coupling
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Abstract: Fe3O4@SiO2 nanoparticles were prepared by hydrolysis of TEOS in the presence of Fe3O4 nanoparticles that were synthesized through co-precipitation procedure. Then, thiamine hydrochloride (VB1) was covalently connected with silica to provide a biodegradable, nontoxic and inexpensive NHC ligand for the formation of complex with palladium. This magnetic bionanocatalyst was characterized using FT-IR, XPS, FE-SEM, TEM, EDX, XRD, VSM, TGA and ICP-AES analysis. The Fe3O4@SiO2@VB1-Pd was found as a magnetically separable and highly active catalyst for the Suzuki coupling reactions of various aryl halides with substituted phenylboronic acids. Under appropriate conditions, all reactions afforded the desired products in excellent yields at short reaction times. Moreover, this catalyst can be easily recovered by using a magnetic field and directly reused for five times in this cross coupling with good yield and suitable time. Graphical Abstract: [Figure not available: see fulltext.]
- Rafiee, Fatemeh,Mehdizadeh, Nasrin
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p. 1345 - 1354
(2018/03/28)
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- Sublimable bis(β-iminoenolate)palladium(II) complexes and their application as catalysts in Suzuki-Miyaura reactions
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The Pd(II) complexes strongly chelated by two β-iminoenolate ligands were easily synthesized in only two steps, and purified based on their sublimable and highly stable property. The Pd(II) complexes anchored on a silica surface showed good catalytic activity in Suzuki-Miyaura reactions (up to 99% yield with 0.05 mol% catalyst). They tolerated a wide range of temperature (rt~110 °C) and various solvents, and could be reused multiple times after simple recovering process.
- Kim, Mi Jin,Jung, Myung Jin,Kim, Yeong Joon,Sung, Ha Kyoung,Lee, Ju Young,Ham, Sung Jin,Park, Chan Pil
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supporting information
p. 2989 - 2993
(2018/07/02)
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- Oxidative and Reductive Cross-Coupling Reactions Catalyzed by an Anionic "ligandless" Palladium Complex
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The anionic complex [NBu4][Pd(DMSO)Cl3], which can be synthesized on a gram scale in a single step starting from commercially available starting materials, has been shown to be an active catalyst in the Mizoroki-Heck reaction of aryl halides. We present two new catalytic applications of this complex: the base-free oxidative Heck reaction and the reductive homodimerization of aryl halides. This complex outperformed other palladium salts. In the latter reaction, the catalyst loading could be reduced to 0.01 mol %. The scope of the reactions has been explored, demonstrating the potential of the anionic palladium complex in these catalytic transformations.
- Schroeter, Felix,Lerch, Swantje,Strassner, Thomas
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supporting information
p. 1614 - 1621
(2019/01/04)
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- Au-Pd bimetallic nanoparticles supported on a high nitrogen-rich ordered mesoporous carbon as an efficient catalyst for room temperature Ullmann coupling of aryl chlorides in aqueous media
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An ionic liquid derived highly nitrogen-rich mesoporous carbon supported Au-Pd alloy was found to be an efficient and recyclable catalyst for the Ullmann coupling reaction of various aryl chlorides at room temperature in aqueous media.
- Karimi, Babak,Barzegar, Hossein,Vali, Hojatollah
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p. 7155 - 7158
(2018/07/05)
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- WEPA: a bio-derived medium for added base, π-acid and ligand free Ullmann coupling of aryl halides using Pd(OAc)2
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A bio-derived sustainable medium based on water extract of pomegranate ash (WEPA) has, for the first time, been developed for the homocoupling of aryl halides under palladium-assistance. Avoiding the requirement of an external base, ligand and π-acid, the use of the proposed renewable medium offers remarkable attributes like wide substrate scope, good to nearly quantitative yields of biphenyls with exceptional chemoselectivity and scale up viability.
- Lakshmidevi, Jangam,Appa, Rama Moorthy,Naidu, Bandameeda Ramesh,Prasad, S. Siva,Sarma, Loka Subramanyam,Venkateswarlu, Katta
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supporting information
p. 12333 - 12336
(2018/11/30)
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- The β-cyclodextrin decorated with palladium nanoparticles without pretreatment: An efficient heterogeneous catalyst for biaryls synthesis
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β-Cyclodextrin decorated with palladium nanoparticles (PdNPs@β-CD) without pretreatment led to a suitable catalyst for the biaryls synthesis in water. A simple and straightforward method was developed for the preparation of PdNPs@β-CD as a green catalyst. The prepared catalyst was characterized by Fourier-transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), X-ray diffraction (XRD), atomic absorption spectroscopy (AAS), transmission electron microscopy (TEM), and energy-dispersive X-ray spectroscopy (EDS) measurements. It was found that PdNPs@β-CD exhibits high performance in Ullmann, Suzuki and Hiyama coupling reactions.
- Feiz, Afsaneh,Loni, Masood,Naderi, Soheila,Bazgir, Ayoob
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- Synthesis of gold nanoparticles decorated on sulfonated three-dimensional graphene nanocomposite and application as a highly efficient and recyclable heterogeneous catalyst for Ullmann homocoupling of aryl iodides and reduction of p-nitrophenol
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Gold nanoparticles were decorated onto sulfonated three-dimensional graphene (3DG-SO3H) through spontaneous chemical reduction of HAuCl4 by 3DG-SO3H. This nanocomposite exhibited excellent catalytic activity for the synthesis of symmetric biaryls via the Ullmann homocoupling of aryl iodides in an aqueous medium. Additionally, this nanocomposite was used as a catalyst for the reduction of p-nitrophenol to p-aminophenol. The catalyst could be used more than six times successively without significant deactivation.
- Dabiri, Minoo,Kashi, Seyede Razie Banifatemi,Lehi, Noushin Farajinia,Bashiribod, Sahareh
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- A practical method for heterogeneously-catalyzed Mizoroki–Heck reaction: Flow system with adjustment of microwave resonance as an energy source
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The microwave-assisted and continuous-flow Mizoroki–Heck reaction using a heterogeneous palladium catalyst supported on the anion-exchange resin DIAION WA30 (7% Pd/WA30) is described. The microwave resonance is finely adjusted to 2.4 GHz according to the electric permittivity of the reaction medium for efficient heating. Organic solvents, such as acetonitrile, N,N-dimethylacetamide, and toluene, can be sufficiently heated even with a low intensity of microwave irradiation in a 7% Pd/WA30-packed, glass tube-shaped catalyst cartridge, which was designed based on the electric permittivity of the solvents. The catalyst cartridge can be continuously reused at least 5 runs without exchange.
- Ichikawa, Tomohiro,Mizuno, Masahiro,Ueda, Shun,Ohneda, Noriyuki,Odajima, Hiromichi,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
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supporting information
p. 1810 - 1816
(2018/03/07)
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- Synthesis and characterization of copper nanoparticles on walnut shell for catalytic reduction and C-C coupling reaction
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Walnut shell-stabilized copper nanoparticles (CuNP/WS) were successfully prepared by a simple reaction of copper sulfate and Sodium borohydride. Formation of copper nanoparticles in this bio-nanocomposite was observed by transmission electron microscopy (TEM) and energy dispersive X-ray spectroscope (EDX). CuNP/WS was found to be an efficient, inexpensive, easy to prepare, green and reusable catalyst in the reduction of aromatic nitro and nitrile compounds to their corresponding amines with NaBH4 at 35 °C in aqueous medium. We continued our studies on the application of this nanocomposite in the classic Ullman reaction to synthesize biaryl. This method has the advantages of high yields, elimination of expensive stabilizer and homogeneous catalysts, simple methodology and easy work up. The catalyst can be recovered from the reaction mixture and reused several times without any significant loss of catalytic activity.
- Zamani, Asghar,Poursattar Marjani, Ahmad,Nikoo, Abbas,Heidarpour, Mojtaba,Dehghan, Ahmad
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p. 176 - 181
(2018/09/25)
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- Palladium-mediated radical homocoupling reactions: A surface catalytic insight
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In this contribution, we report a palladium nanoparticle-promoted reductive homocoupling of haloarenes that proceeds efficiently to produce corresponding bis-aryls in moderate to excellent yields using relatively low catalyst loading (1 mol%), and exhibits broad functional group tolerance. This work sheds light on how the surface state of Pd(0) nanoparticles plays a crucial role in the reactivity of catalytic systems. Notably, the appropriate choice of palladium salts for the preparation of the preformed nanocatalysts was a key parameter having a major impact on the catalytic activity; thus, the effect of halide anions on the reactivity of the as-prepared palladium nanoparticles could be assessed, with iodide anions being capable of inhibiting the corresponding homocoupling reaction. The homocoupling reaction mechanism has been further studied by means of radical trap and electron paramagnetic resonance (EPR) experiments, revealing that the reaction proceeds via radical intermediates. Taking into account these data, a plausible reaction mechanism based on single-electron transfer processes on the palladium nanoparticle surface is discussed.
- Favier, Isabelle,Toro, Marie-Lou,Lecante, Pierre,Pla, Daniel,Gómez, Montserrat
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p. 4766 - 4773
(2018/09/29)
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- Pd-poly(N-vinyl-2-pyrrolidone)/MCM-48 nanocomposite: a novel catalyst for the Ullmann reaction
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Abstract: Homocoupling of aryl halides (Ullmann-type reaction) promoted by a Pd-poly(N-vinyl-2-pyrrolidone)/MCM-48 (Pd–PVP/MCM-48) nanocomposite catalyst is described. In situ polymerization method was employed to prepare composite poly(N-vinyl-2-pyrrolidone)/MCM-48 (PVP/MCM-48) which was used as a support for palladium nanoparticles obtained by reducing Pd(OAc)2 with hydrazine hydrate. FT-IR, XPS, XRD, UV–Vis, SEM, and BET techniques were used to study the chemical and physical properties of the catalyst. The catalytic performance of this heterogeneous catalyst was specified for Ullmann-type reaction between aryl halies in DMF. The catalyst was good with regard to its stability and it can be reused up to six times without significant loss of its activity.
- Mosaddegh, Neda,Yavari, Issa
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p. 2013 - 2021
(2018/07/29)
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- Room-temperature borylation and one-pot two-step borylation/Suzuki-Miyaura cross-coupling reaction of aryl chlorides
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A highly efficient room-temperature borylation strategy of aryl chlorides is described. Utilizing Buchwald's second-generation preformed catalyst, boronate esters were obtained for a wide range of substrates in high yield. The method was also applied to Suzuki-Miyaura cross-coupling reaction in a one-pot two-step sequential manner, providing a facile and convenient access to the direct synthesis of biaryl compounds from aryl chlorides.
- Ji, Hong,Wu, Li-Yang,Cai, Jiang-Hong,Li, Guo-Rong,Gan, Na-Na,Wang, Zhao-Hua
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p. 13643 - 13648
(2018/04/24)
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- Long-Lived Charge-Transfer States of Nickel(II) Aryl Halide Complexes Facilitate Bimolecular Photoinduced Electron Transfer
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Here we investigate the photophysics and photochemistry of Ni(II) aryl halide complexes common to cross-coupling and Ni/photoredox reactions. Computational and ultrafast spectroscopic studies reveal that these complexes feature long-lived 3MLCT excited states, implicating Ni as an underexplored alternative to precious metal photocatalysts. Moreover, we show that 3MLCT Ni(II) engages in bimolecular electron transfer with ground-state Ni(II), which enables access to Ni(III) in the absence of external oxidants or photoredox catalysts. As such, it is possible to facilitate Ni-catalyzed C-O bond formation solely by visible light irradiation, thus representing an alternative strategy for catalyst activation in Ni cross-coupling reactions.
- Shields, Benjamin J.,Kudisch, Bryan,Scholes, Gregory D.,Doyle, Abigail G.
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supporting information
p. 3035 - 3039
(2018/03/08)
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- Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water
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N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.
- Ramakrishna,Dastagiri Reddy
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supporting information
p. 8598 - 8610
(2017/07/12)
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- Bimetallic Au-Pd nanochain networks: Facile synthesis and promising application in biaryl synthesis
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A simple and facile method is described for the morphology-controlled synthesis of bimetallic Au-Pd alloyed nanochain networks (NNCs) that show high catalytic performance for the Ullmann intermolecular homocoupling of aromatic or alkyl halides (X = I, Br, Cl) in aqueous media and can be reused at least five times, which can also be applied to intramolecular homocoupling.
- Wang, Zheng-Jun,Wang, Xia,Lv, Jing-Jing,Feng, Jiu-Ju,Xu, Xinhua,Wang, Ai-Jun,Liang, Zhiwu
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p. 3894 - 3899
(2017/07/12)
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- Ullmann homocoupling of aryl iodides catalyzed by gold nanoparticles stabilized on magnetic mesoporous silica
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Abstract: We demonstrated a convenient new procedure of the Ullmann homocoupling reaction for the synthesis of symmetrical biaryls via homocoupling of aryl iodides over a recyclable gold catalyst comprising Au nanoparticles supported on functional magnetic mesoporous silica (α-Fe2O3)-MCM-41-HS-Au. The catalyst was easily separated by an external magnet, and the recovered catalyst was reused in six successive reaction cycles without any significant loss of activity. So, using this catalyst is affordable. Also, the reaction time is much shorter than a few previously reported work. Graphical Abstract: [Figure not available: see fulltext.]
- Rostamizadeh, Shahnaz,Estiri, Hamid,Azad, Mohammad
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p. 1005 - 1010
(2017/03/11)
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- Heck arylation of allyl alcohol catalyzed by Pd(0) nanoparticles
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Pd(0) nanoparticles ca. 2 nm in diameter were obtained by the reduction of PdCl2 and Pd(OAc)2 in water at 80 °C in the presence of a PVP-stabilizing polymer. Pd(0) NPs were successfully used in the Heck coupling of allyl alcohol with iodo- and bromobenzenes. Iodobenzenes reacted under solventless conditions or in DMF solution producing 3-arylpropanals and 2-arylpropanals as the main products. The same products were obtained in the reaction of bromobenzene in TBAB as the reaction medium. The stability of Pd(0) NPs was evidenced in recycling experiments. Similar Heck coupling results were also obtained with the palladium compounds PdCl2(cod) and Pd(OAc)2 under the same conditions.
- Tarnowicz, Stanis?awa,Alsalahi, Waleed,Mieczyńska, Ewa,Trzeciak, Anna M.
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p. 5605 - 5612
(2017/08/26)
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- Polydopamine nanofilms as visible light-harvesting interfaces for palladium nanocrystal catalyzed coupling reactions
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Light-harvesting material is of great importance for the efficient use of solar energy to drive catalytic reactions in chemistry. We herein report mussel-inspired polydopamine nanofilms as light-harvesting interfaces for heterogeneous palladium catalyzed coupling reactions under irradiation from visible light. Our strategy includes the in situ growth of palladium nanocrystals on a polydopamine nanofilm to prepare photocatalysts and photocatalytic Suzuki coupling reactions involving a broad range of aryl bromides/iodides and arylboronic acid substrates. The polydopamine based photocatalysts could be supported on various carriers regardless of size or morphology, thus they are easily recycled and reused. A plausible photocatalytic mechanism has been proposed including light-harvesting, photoelectron-hole separation and transfer processes. This strategy also has potential for other noble metals such as platinum, indium and gold photocatalytic organic reactions such as couplings, reductions and oxidations.
- Xie, Aming,Zhang, Kun,Wu, Fan,Wang, Nana,Wang, Yuan,Wang, Mingyang
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p. 1764 - 1771
(2016/04/05)
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- Cooperative effects of lanthanides when associated with palladium in novel, 3D Pd/Ln coordination polymers. Sustainable applications as water-stable, heterogeneous catalysts in carbon-carbon cross-coupling reactions
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Three novel porous heterobimetallic coordination polymers, [Ln2Pd3(BPDC)2(HBPDC)2(μ2-O)Cl4(H2O)6·nH2O]m (Ln = Pr, n = 5 (1), Ln = Gd, n = 4 (2), and Ln = Tb, n = 4 (3)), were readily prepared by combining Pd(II) and Ln(III) with 2,2′-bipyridine-4,4′-dicarboxylic acid (H2BPDC) as a heteroleptic ligand, under hydrothermal conditions, and structurally characterized by means of single-crystal X-ray diffraction, FT-IR, powder X-ray diffraction, elemental analysis and thermogravimetric (TG) techniques. Single-crystal X-ray diffraction examination showed that 1-3 have similar 3D frameworks, connected via hydrogen bonding interactions, and consisting of three distinct types of building blocks: Pd(BPDC)Cl2, Pd(HBPDC)2 and a Ln dimer (Ln2O15). The new isostructural, air and water stable coordination polymers, resulting from association of lanthanides with palladium, exhibited superior but distinct capabilities as eco-friendly heterogeneous catalysts in Suzuki-Miyaura, Heck and Sonogashira cross-couplings, under green reaction conditions. Supramolecular, solid catalysts 1-3 have been recovered quantitatively from the reaction mixtures by simple filtration. Also importantly, their sustainability, utility and cost-effectiveness have been demonstrated by recycling experiments with catalyst 1 in Suzuki-Miyaura, proceeding practically without loss of activity after four runs.
- You, Lixin,Zong, Wenhui,Xiong, Gang,Ding, Fu,Wang, Shuju,Ren, Baoyi,Dragutan, Ileana,Dragutan, Valerian,Sun, Yaguang
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- 4,4'-bis(2-bromoacetyl) biphenyl synthesizing method
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The invention discloses a 4,4'-bis(2-bromoacetyl) biphenyl synthesizing method. The method comprises the following steps of 1, adding methylene dichloride and anhydrous aluminum chloride into a reacting kettle, dropwise adding acetyl chloride after cooling, after finishing adding the acetyl chloride, continuously dropwise adding methylene dichloride solution of biphenyl; 2, warming to carry out friedel-crafts reaction after finishing adding the methylene dichloride solution, adding water after finishing the reaction, concentrating, crystallizing and drying to obtain a product of 4.4-diacetyl biphenyl; 3, adding the 4.4-diacetyl biphenyl into acetic acid and then adding bromine to carry out substitution reaction; 4, filtering, concentrating and crystallizing to obtain the 4,4-bis(2-bromoacetyl) biphenyl after finishing the reaction. By means of the method, the obtained product is higher in both purity and yield.
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Paragraph 0028; 0029
(2017/01/02)
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- Palladium-Polypyrrole Nanocomposites Pd@PPy for Direct C-H Functionalization of Pyrroles and Imidazoles with Bromoarenes
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Palladium-polypyrrole nanocomposites (Pd@PPy) with unique combination of high palladium dispersion (nanoparticle size 2.4 nm) and high palladium content (35 wt%) are efficient catalysts for the selective arylation of substituted pyrroles and imidazoles with either activated or deactivated aryl bromides. The performances of the recoverable supported palladium catalyst matches the best performances of homogeneous systems based on Pd(OAc)2 at 0.5-0.2 mol%, and largely overwhelm the classical Pd/C catalyst.
- Bizouard, Pierre,Testa, Christelle,Zinovyeva, Veronika A.,Roger, Julien,Hierso, Jean-Cyrille
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supporting information
p. 1227 - 1231
(2016/05/10)
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- Cobalt-Catalyzed Oxidative Homocoupling of Arylzinc Species
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A novel procedure for the synthesis of functionalized symmetrical biaryl compounds is described. The reaction proceeds via the oxidative homocoupling of arylzinc species formed by cobalt catalysis in the presence of air or p-benzoquinone depending on the nature of the functional group.
- Bourne-Branchu, Yann,Moncomble, Aurélien,Corpet, Martin,Danoun, Gregory,Gosmini, Corinne
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p. 3352 - 3356
(2016/09/12)
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