- Improved Sonogashira C-C coupling through clay supported palladium complexes with tridentate pincer bis-carbene ligands
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Highly active recyclable Pd catalysts modified with a rigid C,N,C-tridentate pincer carbene ligand were successfully applied to the coupling of aryl halides with terminal acetylenes. The immobilization of Pd(II) complexes onto clays has beneficial effects
- Mas-Marzá, Elena,Segarra, Anna M.,Claver, Carmen,Peris, Eduardo,Fernandez, Elena
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- Highly active thiol-functionalized SBA-15 supported palladium catalyst for Sonogashira and Suzuki-Miyaura cross-coupling reactions
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Highly ordered mesoporous silica SBA-15 with pendent 3-mercaptopropyl groups has been prepared by condensation of surface silanols and (3-mercaptopropyl)trimethoxysilane. Treatment of the mercaptopropylated SBA-15 with (CH3CN)2PdCl2 gave a heterogeneous Pd-catalyst. The immobilized Pd-catalyst served as an efficient heterogeneous catalyst for Sonogashira and Suzuki-Miyaura cross coupling reactions of aryl halides. Furthermore, the SBA-15 supported Pd-catalyst was recovered by a simple filtration from the reaction mixture and reused five times without significant loss of its catalytic activity. This journal is
- Sarkar, Shaheen M.,Rahman, Md. Lutfor,Yusoff, Mashitah Mohd
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- Water-medium organic reactions catalyzed by active and reusable Pd/Y Heterobimetal-organic framework
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A Pd/Y heterobimetallic MOF (denoted as Pd/Y-MOF) catalyst is synthesized by coordination of Pd(II) and Y(III) with 2,2′-bipyridine-5,5′- dicarboxylate acid (bpydc) under microwave irradiation condition and is characterized by XRD Rietveld refinement, FTIR, Raman, TG-DTA, and XPS. It is shown that the 3D extended framework is constructed by linking Pd(bpydc)Cl 2 building blocks via Y(III) coordinating to carboxylic groups. Pd/Y-MOF exhibits higher catalytic activity than Pd(bpydc)Cl2 in Suzuki-Miyaura coupling reaction and Sonogashira reaction owing to the highly dispersed Pd(II) sites in the layered structure of Pd/Y-MOF and the cooperative effect between Pd(II) and Y(III). The heterogeneity studies provide mechanistic evidence that the reaction proceeds on the surface of Pd(II) ions in the crystal framework. Thus, Pd/Y-MOF exhibits impressive size selectivity toward substrates. With the small-sized reactants, it displays comparable activities with Pd(OAc)2 homogeneous catalyst. However, extremely poor activity in Suzuki-Miyaura coupling reaction with bulk substrates 1-iodonaphthalene and 4-(tert-butyl) iodobenzene is observed due to the inhibition of diffusion into the micropore channels. In addition, Pd/Y-MOF can be easily recycled and reused owing to the high stability of the framework formed by coordination of Y(III) with carboxylic group. The incorporation of Pd(II) into the crystal framework of Pd/Y-MOF prohibits the leaching of Pd(II) active species.
- Huang, Jinping,Wang, Wei,Li, Hexing
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- Synthesis and characterization of mesoporous Pd(II) organometal nanoplatelet catalyst for copper-free Sonogashira reaction in water
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Periodic mesoporous organopalladium(II)-bridged silica with platelet morphology (Pd(II)-PMO-P) was synthesized by the co-condensation of TEOS and Pd[PPh2(CH2)2Si(OC2H5)3]2Cl
- Zhu, Fengxia,Zhao, Pusu,Li, Qiaoqi,Yang, Didi
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- Effect of addition of iron on morphology and catalytic activity of PdCu nanoalloy thin film as catalyst in Sonogashira coupling reaction
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Palladium-supported catalysts are complex assemblies with a challenging preparation. Minor changes in their preparation conditions can affect the activity, selectivity and lifetime of these catalysts. PdCuFe nanoparticle (NP) thin films were supported on
- Hoseini, S. Jafar,Aramesh, Nahal,Bahrami, Mehrangiz
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- Pd embedded in chitosan microspheres as tunable soft-materials for Sonogashira cross-coupling in water-ethanol mixture
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Easy shaping of chitosan (CS) as porous self-standing nanofibrillar microspheres allows their use as a palladium carrier. Amino-groups on CS enable the modulation of Pd coordination, giving rise to three different support-catalyst interactions: weakly-coo
- Frindy, Sana,Primo, Ana,Lahcini, Mohamed,Bousmina, Mosto,Garcia, Hermenegildo,El Kadib, Abdelkrim
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- Self-Generation of Surface Roughness by Low-Surface-Energy Alkyl Chains for Highly Stable Superhydrophobic/Superoleophilic MOFs with Multiple Functionalities
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We transformed the hydrophilic metal–organic framework (MOF) UiO-67 into hydrophobic UiO-67-Rs (R=alkyl) by introducing alkyl chains into organic linkers, which not only protected hydrophilic Zr6O8 clusters to make the MOF interspace
- Zhu, Neng-Xiu,Wei, Zhang-Wen,Chen, Cheng-Xia,Wang, Dawei,Cao, Chen-Chen,Qiu, Qian-Feng,Jiang, Ji-Jun,Wang, Hai-Ping,Su, Cheng-Yong
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- Preparation and catalytic properties of the triphenylarsine and triphenylstibine-stabilized tri-heteroleptic NHC–Pd?allyl complexes
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A series of triphenylarsine and triphenylstibine-stabilized tri-heteroleptic NHC–Pd?allyl complexes were synthesized and characterized. The solid-state structures of the complexes shown mononuclear carbene palladium complexes, in which, each palladium cen
- Yang, Jin
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- An efficient protocol for copper- and amine-free Sonogashira reactions catalyzed by mononuclear palladacycle complexes containing bidentate phosphine ligands
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An efficient protocol for copper- and amine-free Sonogashira coupling of aryl halides with phenylacetylene in mild reaction conditions under air is reported using moisture/air-stable and robust palladacycle phosphine complexes as catalyst precursors. The use of 0.001 mol% catalysts in the presence of Cs2CO3 allows the coupling reaction to proceed with moderate to good yields. Also, 31P NMR studies showed that palladacycle 1 can be reduced to zerovalent palladium in methanol, by forming dppe dioxide.
- Sabounchei, Seyyed Javad,Ahmadi, Mohsen
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- A tyrosine-rich peptide induced flower-like palladium nanostructure and its catalytic activity
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A specifically designed peptide, Tyr-Tyr-Ala-His-Ala-Tyr-Tyr (YYAHAYY), induced the formation of a flower-like palladium (Pd) nanostructure by controlling the size and shape of nanoparticles (NPs). The flower-shaped Pd NPs showed excellent catalytic activ
- Kim, Young-O,Jang, Hyung-Seok,Kim, Yo-Han,You, Jae Myoung,Park, Yong-Sun,Jin, Kyoungsuk,Kang, Onyu,Nam, Ki Tae,Kim, Jung Won,Lee, Sang-Myung,Lee, Yoon-Sik
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- Nano tetraimine Pd(0) complex as an efficient catalyst for phosphine-free Suzuki reaction in water and copper-free Sonogashira reaction under aerobic conditions
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A nano tetraimine Pd(0) complex catalyst was successfully used as an efficient heterogeneous catalyst for the phosphine-free palladium-catalysed Suzuki coupling reaction in water at 80 °C. This nano tetraimine Pd(0) complex was also used for copper-free Sonogashira reaction in dimethylformamide at 100 °C. The catalyst was easily recovered from the reaction mixture by centrifugation and reused for at least six cycles without any significant loss in its catalytic activity. Analysis of the reaction mixture using inductively coupled plasma analysis showed that leaching of palladium from the catalyst was negligible. The reactions can be performed efficiently for aryl iodides, bromides and also chlorides.
- Mandegani, Zeinab,Asadi, Mozaffar,Asadi, Zahra
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- Hybrid hydrogels loaded with palladium nanoparticles – Catalysts for environmentally-friendly Sonogashira and Heck cross-coupling reactions
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Palladium nanoparticles (PdNPs) were encapsulated within hybrid hydrogels made from an acylhydrazide-functionalised 1,3:2,4-dibenzylidene sorbitol (DBS-CONHNH2) low-molecular-weight gelator (LMWG) combined with agarose polymer gelator via in situ reduction of Pd(II). These heterogeneous gel-phase catalysts were successfully applied for copper-, amine- and phosphine-free Sonogashira cross-coupling reactions under environmentally-friendly conditions without the need for inert atmosphere reaction conditions. The PdNP-loaded gel was reused in Sonogashira couplings up to at least five times with no adverse effect on yield. The performance of solvated PdNP-loaded gel catalysts was compared with the dried xerogels. The xerogels can be used at higher temperatures, enhancing reaction kinetics albeit lowering reaction selectivity, but unlike the solvated gels, were unable to be easily recycled and reused. The PdNP-loaded gels also had good activity in Heck reactions, and although longer reaction times or higher temperatures were required than for the Sonogashira reaction, the reaction conditions were mild for a Heck coupling. In summary, we demonstrate a ‘waste-to-wealth’ methodology in which Pd(II) ‘waste’ is converted into a valuable gel-phase catalyst that can be used for green Sonogashira and Heck cross-coupling reactions.
- Slavik, Petr,Smith, David K.
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- Phosphine free SBA-15-EDTA-Pd highly active recyclable catalyst: Synthesis characterization and application for Suzuki and Sonogashira reaction
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Phosphine obstructed highly efficient and reusable SBA-15-EDTA-Pd(11) has been synthesized by anchoring a Pd-EDTA complex over the surface of organo-functionalized SBA-15. The physiochemical properties of the organo-functionalized catalyst were analyzed b
- Sharma, Priti,Singh
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- One-pot Sonogashira–Hydroarylation reaction catalyzed by anionic palladium complexes in an aqueous medium
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It was found that anionic Pd(II) complexes of type [CA]2[PdCl4] and [CA]2[Pd2Cl6] (CA = imidazolium or pyridinium cation) are effective catalysts for copper-free Sonogashira coupling in an aqueous med
- Dziadas, M.,Trzeciak, A. M.,Wójcik, E.
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supporting information
(2022/01/26)
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- Pd nanoparticles catalyst supported on TMU-16-NH2 metal-organic framework for Sonogashira cross-coupling reaction
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The current article presented the synthesis and characterization of a novel, unique, and effective heterogeneous catalytic system, based on a metal-organic framework named Pd@TMU-16-NH2 with high catalytic performance. Also, the application of
- Alinezhad, Heshmatollah,Ghasemi, Shahram,Kiani, Ameneh
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- Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction
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Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been es
- Ghodsinia, Sara S. E.,Akhlaghinia, Batool,Jahanshahi, Roya
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p. 3217 - 3244
(2021/05/17)
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- Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions
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Two bis-imidazolium salts LH2·Cl2 and LH2·(PF6)2 with acylated piperazine linker and two N-heterocyclic carbene (NHC) silver(I) and palladium(II) complexes [L2Ag2](PF6)2 (1) and [L2Pd2Cl4] (2) were prepared. The crystal structures of LH2·Cl2 and 1 were confirmed by X-ray analysis. In 1, one 26-membered macrometallocycle was generated through two silver(I) ions and two bidentate ligands L. The catalytic activity of 2 was investigated in Sonogashira, Heck-Mizoroki and Suzuki-Miyaura reactions. The results displayed that these C—C coupling reactions can be smoothly carried out under the catalysis of 2.
- Liu, Qingxiang,Zhang, Xiantao,Zhao, Zhixiang,Li, Xinying,Zhang, Wei
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supporting information
p. 605 - 613
(2021/02/01)
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- Decorated palladium nanoparticles on mesoporous organosilicate as an efficient catalyst for Sonogashira coupling reaction
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Abstract: Reforming mesoporous silica was provided by the reaction of SBA‐15 with (3-aminopropyl)triethoxysilane, the product of which was treated with furfural to give SBA-propyl-imine-furan. In the next step, palladium chloride was attached to the funct
- Mohajer, Fatemeh,Mohammadi Ziarani, Ghodsi,Badiei, Alireza
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p. 589 - 601
(2020/09/17)
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- Introduction of a Recyclable Basic Ionic Solvent with Bis-(NHC) Ligand Property and The Possibility of Immobilization on Magnetite for Ligand- and Base-Free Pd-Catalyzed Heck, Suzuki and Sonogashira Cross-Coupling Reactions in Water
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A new versatile and recyclable NHC ligand precursor has been developed with ligand, base, and solvent functionalities for the efficient Pd-catalyzed Heck, Suzuki and Sonogashira cross-coupling reactions under mild conditions. Furthermore, NHC ligand precursor was immobilized on magnetite and its catalytic activity was also evaluated towards the coupling reactions as a heterogeneous catalyst. The NHC ligand precursor was prepared with imidazolium functionalization of TCT followed by a simple ion exchange by hydroxide ions. However, the results revealed an excellent catalytic activity for the both homogeneous and heterogeneous catalytic systems. 1.52?g.cm?3 and 1194 cP was obtained for the density and viscosity of the NHC ligand precursor respectively. On the other hand, the heterogeneous type could be readily recovered from the reaction mixture and reused for several times while preserving its properties. Heterogeneous nature of the magnetic catalyst was studied by hot filtration, mercury poisoning, and three-phase tests. High to excellent yields were obtained for all entries for the both homogeneous and heterogeneous catalysts, which reflects the high consistency of the catalyst. Graphic Abstract: [Figure not available: see fulltext.]
- Min, Qingwang,Miao, Penghua,Chu, Deyu,Liu, Jinghan,Qi, Meijuan,Kazemnejadi, Milad
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p. 3030 - 3047
(2021/02/16)
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- Versatile and an efficient Sonogashira coupling reaction catalyzed with modified Pd-functionalized TMU-16 as a novel and reusable nanocatalyst
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This research paper, reports the preparation of palladium impregnated [Zn2(BDC)2(4-bpdh)]3DMF (Pd@TMU-16) with a simple liquid impregnation-reduction method as a novel and efficient catalyst with the high catalytic performance for co
- Alinezhad, Heshmatollah,Ghasemi, Shahram,Kiani, Ameneh
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- Immobilized Pd on a NHC-functionalized metal-organic FrameworkMIL-101(Cr): An efficient heterogeneous catalyst in the heck and copper-free Sonogashira coupling reactions
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A heterogeneous palladium catalyst system based on immobilization of palladium moieties on a N-heterocyclic carbene (NHC) modified metal organic framework (MOF) was developed for the Heck and copper-free Sonogashira coupling reactions. In order to prepare this catalyst system, first, MIL-101(Cr) was functionalized with NHC moieties through a post synthetic modification (PSM) approach, and then Pd metal was stabilized on the prepered MIL-101(Cr)-NHC substrate. This material was characterized using various microscopic and spectroscopic techniques and then was used as an efficient heterogeneous Pd catalyst system in the Heck and copper-free Sonogashira reactions. Results of the heterogeneity tests showed that the Pd-NHC-MIL-101(Cr) catalyst can efficiently catalyzed these coupling reactions heterogeneously and no remarkable changes observed in the morphology and structure of MIL-101(Cr) template during the reaction progress. Also, existence of palladium nanoparticles immobilized on the MOF structure affirmed by the TEM and XPS analysis confirmed the oxidation state of Pd. A variety of alkene and alkyne derivatives were synthesized in good to excellent yields using this heterogeneous Pd catalyst system under normal conditions. More importantly Pd-NHC-MIL-101(Cr) catalyst was simply recovered from the reaction medium without remarkable decreasing in its catalytic activities after five times of reusability. The ICP analysis showed the very low Pd and Cr metals leaching, representing high stability and applicability of this catalyst in Pd coupling reactions.
- Niknam, Esmaeil,Panahi, Farhad,Khalafi-Nezhad, Ali
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supporting information
(2021/01/12)
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- A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd0 Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope
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Three different Pd0-based heterogeneous catalysts were developed and tested in the Cassar–Heck reaction (i. e., copper-free Sonogashira reaction) aiming at the definition of a waste minimized protocol. The cross-linked polymeric supports used in this investigation were designed to be adequate for different reaction media and were decorated with different pincer-type ionic ligands having the role of stabilizing the formation and dimension of palladium nanoparticles. Among the ionic tags tested, bis-imidazolium showed the best performances in terms of efficiency and durability of the metal catalytic system. Eventually, aqueous acetonitrile azeotrope was selected as the reaction medium as it allowed the best catalytic efficiency combined with easy recovery and reuse. Finally, the synergy between the selected catalyst and reaction medium allowed to obtain highly satisfactory isolated yields of a variety of substrates while using a low amount of metal catalyst. The high performance of the designed POLymeric Ionic TAG (POLITAG)-Pd0, along with its good selectivity achieved in a copper-free process, also led to a simplified purification procedure allowing the minimization of the waste generated as also proven by the very low E-factor values (1.4–5) associated.
- Valentini, Federica,Ferlin, Francesco,Tomarelli, Elena,Mahmoudi, Hamed,Bagherzadeh, Mojtaba,Calamante, Massimo,Vaccaro, Luigi
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p. 3359 - 3366
(2021/07/28)
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- Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent
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Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.
- Karimi, Sabah,Masteri-Farahani, Majid,Niakan, Mahsa,Shekaari, Hemayat
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- Si-Gly-CD-PdNPs as a hybrid heterogeneous catalyst for environmentally friendly continuous flow Sonogashira cross-coupling
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We have reported a waste-minimized protocol for the Sonogashira cross-coupling exploiting the safe use of a CPME/water azeotropic mixture and the utilization of a heterogeneous hybrid palladium catalyst supported onto a silica/β-cyclodextrin matrix in con
- Cravotto, Giancarlo,Ferlin, Francesco,Martina, Katia,Menzio, Janet,Sciosci, Daniele,Vaccaro, Luigi,Valentini, Federica
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supporting information
p. 7210 - 7218
(2021/09/28)
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- Bimetallic Ni/Cu mesoporous silica nanoparticles as an efficient and reusable catalyst for the Sonogashira cross-coupling reactions
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A bimetallic mesoporous system (Ni/Cu-MCM-41) has been developed and evaluated as an efficient catalyst for the Sonogashira cross-coupling reaction, under palladium-free conditions. In this new methodology, a wide range of aryl halides react with phenylacetylene to give the corresponding disubstituted alkynes in good yields. Moreover, the present catalytic system is desired because of its high efficiency, easy preparation, low cost, high activity, and good recyclability.
- Nasresfahani, Zahra,Kassaee, Mohamad Z.
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supporting information
(2021/02/12)
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- NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media
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The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is
- Alavi G., Seyyedeh Ameneh,Nasseri, Mohammad Ali,Kazemnejadi, Milad,Allahresani, Ali,Hussainzadeh, Mahdi
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p. 7741 - 7757
(2021/05/13)
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- Copper(0) nanoparticle catalyzed Z-Selective Transfer Semihydrogenation of Internal Alkynes
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The use of copper(0) nanoparticles in the transfer semihydrogenation of alkynes has been investigated as a lead-free alternative to Lindlar catalysts. A stereo-selective methodology for the hydrogenation of internal alkynes to the corresponding (Z)-alkenes in high isolated yields (86% average) has been developed. This green and sustainable transfer hydrogenation protocol relies on non-noble copper nanoparticles for reduction of both electron-rich and electron-deficient, aliphatic-substituted and aromatic- substituted internal alkynes. Polyols, such as ethylene glycol and glycerol, have been proven to act as hydrogen sources, and excellent stereo- and chemoselectivity have been observed. Enabling technologies, such as microwave and ultrasound irradiation are shown to enhance heat and mass transfer, whether used alone or in combination, resulting in a decrease in reaction time from hours to minutes. (Figure presented.).
- Moran, Maria Jesus,Martina, Katia,Bieliunas, Vidmantas,Baricco, Francesca,Tagliapietra, Silvia,Berlier, Gloria,De Borggraeve, Wim M.,Cravotto, Giancarlo
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supporting information
p. 2850 - 2860
(2021/05/06)
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- Xantphos-coordinated palladium dithiolates: Highly efficient catalyst for decarboxylative Sonogashira reaction into corresponding alkynes
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This work reports Xantphos-coordinated palladium dithiolate complexes as catalysts for decarboxylative Sonogashira coupling reaction of phenyl propiolic acid and 2-butynoic acid with various iodoarenes. These palladium aryl dithiolate complexes were synthesized and characterized by 1H and 31P nuclear magnetic resonance (NMR) spectroscopy, melting point, and elemental analysis (CHNS). Synthetic utility for the reported protocol is explored for the effect of various functional groups on the yield of corresponding heteroaryl alkynes. The current protocol showed excellent catalytic activity towards decarboxylative alkynylation reaction with high turn-over number (TON) up to 105 and turn-over frequency (TOF) up to 104 h?1. The catalyst could be recycled up to six recycles without losing its catalytic activity. The in situ generation of palladium nanoparticles (PdNPs) was observed after the third recycle, and the amount was significant after the sixth recycle, which were confirmed and characterized by powder X-ray diffraction (XRD), scanning electron microscope (SEM), and energy-dispersive X-ray (EDX) analysis and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of the reaction is attributed to the formation of PdNPs.
- Lokolkar, Manjunath S.,Mane, Pravin A.,Dey, Sandip,Bhanage, Bhalchandra M.
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- Ultrafine Pd nanoparticles loaded benzothiazole-linked covalent organic framework for efficient photocatalytic C-C cross-coupling reactions
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We proposed a strategy that a benzothiazole-linked covalent organic framework (TTT-COF) was used as a substrate to prepare metal composite photocatalyst Pd NPs?TTT-COF. Firstly, benzothiazole linked TTT-COF exhibited superior chemical stability and photoresponse. Moreover, a finer particle size (2.01 nm) and more uniform distribution of Pd NPs were observed in Pd NPs?TTT-COF owing to the binding interaction between Pd NPs and S in benzothiazole groups. Pd NPs?TTT-COF exhibited superior efficiency and reusability in photocatalytic C-C cross-coupling reactions. Mechanism study suggested that photogenerated electrons and holes on TTT-COF played important roles in these reactions. This journal is
- Cai, Yaqi,Niu, Hongyun,Xu, Lin,Yang, Yongliang,Zhang, Hui,Zhao, Weijia
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p. 29402 - 29407
(2020/10/02)
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- A new approach to large scale production of dimethyl sulfone: A promising and strong recyclable solvent for ligand-free Cu-catalyzed C-C cross-coupling reactions
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Dimethyl sulfone (DMSN) was easily prepared through efficient oxidation of dimethyl sulfoxide (DMSO) and used as a strong and green solvent for organic reactions. A mixture of HNO3/NaOCl was used as an oxidizing agent for efficient oxidation of DMSO to DMSN. The effect of DMSN was evaluated for copper-catalyzed coupling reactions. It is worth noting that DMSN could play the role of a ligand for copper ions. A general survey was accomplished for various types of C-C cross-coupling reactions catalyzed by CuI in DMSN in the absence of any ligand. Moderate to good yields were achieved for Sonogashira, Heck, and Suzuki cross-coupling reactions. Finally, DMSN was recovered and reused for several consecutive runs without any loss of its activity.
- Cheng, Shen,Wei, Wei,Zhang, Xingyu,Yu, Hewei,Huang, Mingming,Kazemnejadi, Milad
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p. 2069 - 2076
(2020/04/07)
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- Palladium(II) phthalocyanines efficiently promote phosphine-free Sonogashira cross-coupling reaction at room temperature
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Herein we report that exceptionally simple and inexpensive Pd(II) complexes of phthalocyanines efficiently catalyze direct formation of diphenylacetylenes at ambient conditions with low loading of catalyst (0.5 mol%). Results of this study demonstrate that terminal alkynes reacted mildly with p-substituted aryl bromides at room temperature under Pd and Cu-cocatalysis to give the corresponding phenylacetylenes in yields up to 98%. Also we have examined this catalyst in Sonogashira cross-coupling with aryl chlorides and it was very effective and this reaction at room temperature that there is no examples in recent articles. This protocol represents the first use of palladium phthalocyanine as homogeneous catalyst in the Pd/Cu-promoted Sonogashira reaction. The palladium(II) phthalocyanine complex is significantly more active in Sonogashira cross-coupling between aryl halides and terminal alkynes as compared with traditional catalysts because of absence of palladium black formation through agglomeration of metal particles and deactivation of catalyst.
- Platonova, Yana B.,Tomilova, Larisa G.,Volov, Alexander N.
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p. 224 - 228
(2020/09/17)
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- Palladium(II) complexes containing sterically bulky O, N donor ligands: Synthesis, characterization and catalytic activity in the Suzuki-Miyaura and Sonogashira coupling reactions
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A new class of palladium(II)1-(arylazo)naphtholate complexes of the type [Pd(L1-4)2] containing sterically bulky O, N donor functionalized arylazo ligands has been synthesized. These palladium(II) complexes were characterized by elemental analysis and spectral (FT-IR, UV–Vis, 1H NMR and 13C NMR) studies. The molecular structure of the Palladium(II) complexes [Pd(L1)2] and [Pd(L2)2] were established by X-ray crystallography. These complexes were found to efficiently catalyze the Suzuki-Miyaura coupling of arylboronic acids and aryl halides, and the Sonogashira reaction of aryl halides and phenylacetylene in DMF and i-PrOH media to afford the corresponding C–C coupling products in high yields.
- Nandhini, Raja,Vijayan, Paranthaman,Venkatachalam, Galmari
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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 Pd confined hierarchically conjugated covalent organic polymer for hydrogenation of nitroaromatics: Catalysis, kinetics, thermodynamics and mechanism
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Herein, we propose a fast and scalable synthesis of a triazine based hierarchically conjugated covalent organic polymer under solvent and additive free conditions through a single step process. The synthesized material CCTP (Cyanuric Chloride-Thiourea-Polymer) was thoroughly characterized by various physicochemical techniques. The CCTP exhibited regular sponginess and excellent chemical as well as thermal stability. The solvent and additive free approach for CCTP synthesis provides a sustainable alternative for classical solvothermal methods. The CCTP was immobilized with Pd (0) and subsequently a heterogeneous material Pd&at;CCTP was obtained, which was used as an efficient catalyst for the hydrogenation of nitroarenes. The rate constant and Ea were measured to be 2.08 × 10-2 s-1 and 15.67 kJ mol-1 respectively and thereafter other thermodynamic parameters like ΔH, ΔS and ΔG for the hydrogenation of p-nitrophenol were also calculated. The obtained results indicate that the catalytic hydrogenation of p-nitrophenol is a non-spontaneous and endothermic process. We have also investigated the effect of surfactants (NH4OH, FA, and N2) on the reaction performance, and consequently NH4OH and FA both slow down the reaction while N2 doesn't affect the reaction medium. Further, we calculated the rate constant for the hydrogenation of 2,4-dinitrophenol and 2,4,6-trinitrophenol. An array of nitroarenes were further reduced to extend the substrate scope at RT; high TOFs were observed. Besides, Pd&at;CCTP showed excellent reusability in hydrogenation reactions without evident performance falloff.
- Awasthi, Satish Kumar,Yadav, Deepika
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supporting information
p. 4295 - 4303
(2020/07/30)
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- A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water
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A novel magnetically recyclable bimetallic catalyst was prepared by anchoring imidazolium moiety and PEG chains on Fe3O4 NPs and named as Fe3O4?PEG/Cu-Co. It was found to be a powerful catalyst for the Sonogashira, Suzuki, and C-N cross-coupling reactions in water as a green solvent without the need for any external base. Fe3O4?PEG/Cu-Co was well characterized with FT-IR, FE-SEM, TEM, VSM, EDX, ICP, UV-visible, CV, and XPS analyses. Optimum ranges of parameters such as time, temperature, and amount of catalyst were investigated by Design-Expert 10.0.7 software for C-C Suzuki, Sonogashira, and C-N cross-coupling reactions to find the optimum conditions. The catalyst was compatible with a variety of aryl halides and N-arenes and gave favorable coupling products with good to high yields for all of them. Hot filtration and Hg poisoning tests involving the nanocatalyst revealed the stability, low metal leaching, and heterogeneous nature of the catalyst. Reaction mechanisms were proposed by study of the UV-visible spectra in situ as well as hydroquinone tests during the progress of reactions. In situ XPS analysis was also used to study the reaction mechanism. To prove the synergistic performance of Co and Cu in the catalyst, its various homologues were synthesized and applied to a model reaction separately, and then their catalytic activities were investigated. Finally, the catalyst could be recovered from the reaction mixture simply, and reused for several cycles with a minimum loss in catalytic activity and performance.
- Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat
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p. 10645 - 10660
(2020/09/18)
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- Preparation anchored Pd nanoparticles on glyoxal modified metal- organic framework for Sonogashira coupling reactions
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UIO-66-NH2-Gl?Pd nanocatalyst was successfully synthesized during post-synthetic modification (PSM) method and its application was investigated in the Sonogashira coupling reactions. Initially, UIO-66-NH2 was synthesized and identifi
- Alinezhad, Heshmatollah,Cheraghian, Mansoureh,Ghasemi, Shahram
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- A Pd NP-confined novel covalent organic polymer for catalytic applications
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A novel unsymmetrical covalent organic polymer, COP (1), was designed and characterized using several analytical and spectroscopic techniques. COP (1) was synthesized via the nucleophilic substitution reaction of 2,4,6-trichloro-1,3,5-triazine with p-amin
- Yadav, Deepika,Awasthi, Satish Kumar
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p. 1320 - 1325
(2020/02/04)
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- Fast heck-cassar-sonogashira (hcs) reactions in green solvents
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The replacement of toxic solvents with greener alternatives in Heck-Cassar-Sonogashira (HCS) cross-couplings was investigated. The fine-tuning of the HCS protocol allowed to achieve complete conversions and high speed under mild conditions. N-Hydroxyethylpyrrolidone (HEP) gave the best results. Moreover, the methodology was successfully applied to the synthesis of an intermediate of the anticancer drug Erlotinib, demonstrating the versatility of the new green protocol.
- Cabri, W.,Corbisiero, D.,Daka, A.,Fantoni, T.,Ferrazzano, L.,Martelli, G.,Ricci, A.,Tolomelli, A.,Viola, A.
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supporting information
p. 3969 - 3973
(2020/06/08)
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- Monosubstituted, Anionic Imidazolyl Ligands from N?H NHC Precursors and Their Activity in Pd-Catalyzed Cross-Coupling Reactions
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We report that treatment of several 2-diphenylphosphinoimidazoles with Pd(II) salts generates monosubstituted N?H NHC?Pd complexes via insertion into the C?P bond. Removal of the N?H proton in situ leads to anionic (X-type) or imidazolyl-Pd complexes that are highly stable and catalytically active, achieving up to 340,000 turnovers at 1 ppm catalyst loading in Suzuki-Miyaura reactions. DFT-calculated Tolman electronic parameters for the sterically small ligands suggest that these ligands are significantly more donating than traditional NHCs, which provides a rationale for rapid cross-coupling catalysis. Excellent reactivity is also demonstrated in Sonogashira reactions. (Figure presented.).
- Clark, Kyle J.,Ess, Daniel H.,Jensen, Christopher A.,Kenney, Karissa C.,Larson, Alexandra J. S.,Martinez, Erin E.,Michaelis, David J.,Nazari, S. Hadi,Smith, Stacey J.,Valdivia-Berroeta, Gabriel A.
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supporting information
(2020/07/06)
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- (E)-N-(pyren-1-ylmethylene)benzenamine: efficient promoter for additive-free palladium catalyzed aerobic oxidative coupling of arylboronic acids and terminal alkynes
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Abstract: A highly productive protocol for the synthesis of internal alkynes by the carbon–carbon cross-coupling reactions of electronically different arylboronic acids with substituted phenylacetylenes was described by employing (E)-N-(pyren-1-ylmethylene)benzenamine with Pd(OAc)2. The influence of reaction parameters such as solvent, base and reaction temperature in this carbon–carbon cross-coupling reaction was also investigated. The substrate scope could be expanded to electron-poor alkynes, for which the conventional Sonogashira reaction gives poor yields. Moderate to excellent yield was obtained in the oxidative Sonogashira-type coupling reaction. Graphic abstract: [Figure not available: see fulltext.]
- Lakshmipraba, Jagadeesan,Prabhu, Rupesh Narayana,Dhayabaran, Victor Violet
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p. 3661 - 3669
(2020/04/21)
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- Anthracen-9-ylmethylene-(4-methoxyphenyl)amine: efficient promoter for silver-free palladium-catalyzed aerobic oxidative Sonogashira reactions
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An efficient protocol for the synthesis of unsymmetrical substituted diarylacetylenes by the C(sp2)–C(sp) cross-coupling reactions of substituted phenylacetylenes and electronically different arylboronic acids has been developed. Anthracen-9-ylmethylene-(4-methoxyphenyl)amine was employed as an efficient promoter in this Pd(OAc)2-catalyzed oxidative Sonogashira reaction in air in the absence of silver salt under optimized reaction conditions. The impact of reaction parameters such as solvent, base, reaction temperature and time in this silver-free aerobic oxidative Sonogashira cross-coupling reaction was also evaluated. Electron-deficient phenylacetylenes, which are sluggish coupling partners in the traditional Sonogashira reaction, underwent coupling in this protocol. The catalytic system is inexpensive, effortlessly attainable and highly flexible for functionalized phenylacetylenes and arylboronic acids. Graphic abstract: [Figure not available: see fulltext.].
- Lakshmipraba, Jagadeesan,Prabhu, Rupesh Narayana,Dhayabaran, Victor Violet
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p. 325 - 331
(2020/04/15)
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- A series of (NHC)Pd(N?O)(OAc) complexes: synthesis, characterization and catalytic activities towards desulfinative Sonogashira coupling of arylsulfonyl hydrazides with arylalkynes
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A series of well-defined N-heterocyclic carbene palladium (II) complexes with general formula (NHC)Pd(N?O)(OAc) were prepared through reaction of Pd (NHC)(OAc)2(H2O) with 1-methyl-1H-pyrazole-3-carboxylic acid or 1-methyl-1H-indazole-3-carboxylic acid in the presence of K2CO3. These complexes were then used for desulfinative Sonogashira coupling of arylsulfonyl hydrazides with terminal alkynes. With low catalyst loading, all synthesized palladium compounds exhibited moderate to high catalytic activities for the reactions.
- Lu, Jian-Zhong,Wang, Tian,Yang, Jin,Zhao, Ya-Yu,Zhu, Guang-Hao
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- Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids
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Abstract: The reaction of simple alkynoate salts with isolated arenediazonium tetrafluoroborate salts that had been pre-conditioned with the gold(I) catalyst AuCl(Me2S) led to the formation of cross-coupled products via a decarboxylative Sonogashira reaction process in modest yield and under mild conditions. The major by-product is a defunctionalized aryl moiety stemming from the diazonium salt, which competitively forms via hydrodediazonation. Good functional group tolerance and reaction site selectivity were attained in this limited investigation.
- Abrams, J. N.,Chi, B. K.
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p. 1236 - 1244
(2020/09/17)
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- Preparation method of aryl alkyne catalyzed by visible light
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The invention discloses a simple and convenient method for directly synthesizing an aryl alkyne compound through photoredox catalysis. Aryl fluoroborate diazoate is used as an aryl free radical source, and different types of aryl alkyne are synthesized in situ through a decarboxylation process. A reaction has good functional group tolerability, and a simple domestic visible light source can be used for synthesizing the aryl alkyne of different functional groups under mild, neutral and transition-free metal reaction conditions.
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Paragraph 0050-0053
(2019/11/13)
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- A palladium catalyzed aryl alkyne preparation method
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The invention discloses a palladium catalyzed aryl alkyne of the preparation method, comprises the following steps: in the catalyst, under the action of the ligand and alkali, substituted with aryl sulfonyl chloride alkynoic occurs in the organic solvent escapes suosuo the coupling reaction, after the reaction is finished after treatment to obtain the aryl alkyne. Used in the preparation method of the cheap raw material, the reaction and simple post treatment operation, at the same time, the reaction less side reaction, high yield of the product.
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-
Paragraph 0037; 0038; 0039
(2019/05/21)
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- Porous organic polymer with: In situ generated palladium nanoparticles as a phase-transfer catalyst for Sonogashira cross-coupling reaction in water
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A new Pd nanoparticle loaded and imidazolium-ionic liquid decorated organic polymer of Pd@PTC-POP was readily fabricated via a Pd(PPh3)4 catalysed in situ one-pot Suzuki cross-coupling reaction between imidazolium attached dibromoben
- Dong, Ying,Chen, Yun-Qi,Jv, Jing-Jing,Li, Yue,Li, Wen-Han,Dong, Yu-Bin
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p. 21671 - 21678
(2019/07/30)
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- A BODIPY-functionalized PdII photoredox catalyst for Sonogashira C-C cross-coupling reactions
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We report for the first time a BODIPY-functionalized dichloro(1,10-phenanthroline)palladium(ii) complex as an efficient photoredox catalyst for the Sonogashira C-C cross-coupling between phenylacetylene derivatives and iodobenzene derivatives with yields
- Dissanayake, Komadhie C.,Ebukuyo, Peters O.,Dhahir, Yasser J.,Wheeler, Kraig,He, Hongshan
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p. 4973 - 4976
(2019/05/21)
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- The CuFe2O4@SiO2@ZrO2/SO42-/Cu nanoparticles: An efficient magnetically recyclable multifunctional Lewis/Br?nsted acid nanocatalyst for the ligand- and Pd-free Sonogashira cross-coupling reaction in water
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Herein, the synthesis and application of copper-incorporated sulfated zirconium oxide supported on CuFe2O4 NPs (CuFe2O4@SiO2@ZrO2/SO42-/Cu NPs) as a novel Lewis/Br?nsted acid nanocatalyst were studied for the Sonogashira C-C cross-coupling reaction. The fabricated CuFe2O4@SiO2@ZrO2/SO42-/Cu catalyst exhibited efficient activity for a large variety of aryl iodides/bromides and, most importantly, aryl chlorides in water and in the presence of NaOH as a base in short reaction times. The catalyst was fully characterized by FTIR, TG-DTG, VSM, XRD, EDX, FE-SEM and TEM analyses. A synergetic effect could be considered to have arisen from the various Lewis acid and Br?nsted acid sites present in the catalyst. The efficient incorporation of copper into zirconia provided a robust highly stable hybrid, which prevented any metal leaching, whether from the magnetite moiety and/or Cu sites in the reaction mixture. Moreover, the catalyst was successfully recovered from the mixture by a simple external magnet and reused for at least 9 consecutive runs. Zero metal leaching, stability, consistency with a variety of substrates, fast performance, cost-effectiveness, environmental friendliness, and preparation with accessible and cheap materials are some of the advantages and highlights of the current protocol.
- Nasseri, Mohammad Ali,Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Allahresani, Ali
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p. 20749 - 20759
(2019/07/12)
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- Bis-salophen palladium complex immobilized on Fe3O4@SiO2 nanoparticles as a highly active and durable phosphine-free catalyst for Heck and copper-free Sonogashira coupling reactions
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New Fe3O4@SiO2 core-shell superparamagnetic nanoparticles functionalized by a bis-salophen Schiff base Pd complex were synthesized and employed as an efficient magnetic nanocatalyst in the Heck and Sonogashira cross coupling reactions. The synthesized nanostructures were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), elemental analysis (CHN), cyclic voltammetry (CV), Brunauer-Emmett-Teller analysis (BET), and UV-vis spectroscopy. The morphology and size of the nanoparticles were investigated by FE-SEM and TEM analyses. Furthermore, the magnetic properties of the catalyst were investigated by VSM analysis. The loading content and leaching amounts of palladium on the catalyst were measured by inductively coupled plasma (ICP) analysis. Also, the thermal behavior of this magnetic heterogeneous catalyst was studied using a TGA instrument. This heterogeneous catalytic system showed a good performance in the coupling of aryl halides with alkynes (Sonogashira reaction) as well as aryl halides with alkene derivatives (Heck reaction). High to excellent yields were achieved for these C-C coupling reactions. The catalyst can be simply separated from the reaction media by an external magnet and reused for eight consecutive runs without any significant loss of activity. Finally, the kinetics of the reactions were studied in this work.
- Sardarian, Ali Reza,Kazemnejadi, Milad,Esmaeilpour, Mohsen
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p. 3132 - 3145
(2019/03/06)
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- Green, cost-effective and efficient procedure for Heck and Sonogashira coupling reactions using palladium nanoparticles supported on functionalized Fe3O4@SiO2 by polyvinyl alcohol as a highly active, durable and reusable catalyst
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A novel heterogenized organometallic catalyst was synthesized by coordinating palladium with polyvinyl alcohol-functionalized Fe3O4@SiO2 nanospheres. This novel catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, transmission electron microscope, field emission scanning electron microscope, dynamic light scattering, UV–vis spectroscopy, X-ray photoelectron spectroscopy, energy dispersive X-ray analysis, thermogravimetric analysis and inductively coupled plasma analysis. The prepared palladium nanoparticles supported on polyvinyl alcohol functionalized Fe3O4@SiO2 nanoparticles were successfully applied as a magnetically recyclable catalyst in Heck and Sonogashira coupling reactions in water. They showed remarkable activity toward aryl halides (I, Br, Cl) using very low palladium loading in excellent yields and demonstrated high TONs (mmol of product per mmol of catalyst). Also, the catalyst could be magnetically separated and reused seven times without any appreciable loss of catalytic activity.
- Sardarian, Ali Reza,Eslahi, Hassan,Esmaeilpour, Mohsen
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- Synthesis and structural characterization of palladium(II) 2-(arylazo)naphtholate complexes and their catalytic activity in Suzuki and Sonogashira coupling reactions
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A family of five palladium(II) 2-(arylazo)naphtholate complexes, [PdCl(PPh3)(L)] (L = O, N-donor of bidentate 2-(arylazo)naphtholate ligands), have been synthesized and characterized by elemental analysis and spectral (FT-IR, UV–Vis, 1H-NMR and 13C-NMR) methods. Further, the catalytic efficiency of all the complexes have been investigated for Suzuki and Sonogashira coupling reaction of various aryl halides.
- Munusamy, Sathya,Muniyappan, Premkumar,Galmari, Venkatachalam
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p. 1910 - 1921
(2019/06/17)
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- Gold-Catalyzed Hydrofluorination of Internal Alkynes Using Aqueous HF
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The gold-catalyzed hydrofluorination reaction of internal alkynes using hydrofluoric acid is reported. Notably, those conditions use one of the most economical sources of HF and are free of additional additives. Both symmetrical and unsymmetrical internal alkynes can be utilized, and the use of alkynes bearing a fluorinated group at the propargylic position as substrates allowed for a regioselective hydrofluorination reaction.
- Gauthier, Rapha?l,Mamone, Marius,Paquin, Jean-Fran?ois
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supporting information
p. 9024 - 9027
(2019/11/14)
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- Sequentially Pd/Cu-Catalyzed Alkynylation-Oxidation Synthesis of 1,2-Diketones and Consecutive One-Pot Generation of Quinoxalines
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We report a simple and efficient one-pot synthesis of 1,2-diketones by concatenation of two Pd/Cu-catalyzed processes: Pd0/CuI-catalyzed Sonogashira coupling of terminal alkynes with aryl (pseudo)halides furnishes internal alkynes, which are directly transformed by PdII/CuII-catalyzed Wacker-type oxidation with DMSO and oxygen as dual oxidants to furnish 1,2-diketones. With this efficient, catalyst economical process, various aryl iodides and triflates are efficiently transformed in high yields into symmetrically and unsymmetrically substituted 1,2-diketones with various functional groups. This process can be readily extended to a consecutive one-pot synthesis of quinoxalines in a diversity-oriented fashion.
- Niesobski, Patrik,Martínez, Ivette Santana,Kustosz, Sebastian,Müller, Thomas J. J.
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supporting information
p. 5214 - 5218
(2019/07/31)
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- Synthesis and characterization of a new poly(N–heterocyclic carbene Cu complex) immobilized on nano–silica, (CuII–NHCs)n@nSiO2, and its application as an efficient and reusable catalyst in the synthesis of benzimidazoles,
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The present study describes the synthesis and characterization of a new poly(N–heterocyclic carbene Cu complex) immobilized on nano silica, (CuII–NHCs)n@nSiO2. The (CuII–NHCs)n@nSiO2 dendri
- Khajehzadeh, Mostafa,Moghadam, Majid,Jamehbozorgi, Saeed
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p. 173 - 189
(2018/10/21)
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- Functionalized graphene oxide anchored to Ni complex as an effective recyclable heterogeneous catalyst for Sonogashira coupling reactions
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The Sonogashira cross coupling reaction is an applied method for preparation of diarylethyne compounds from readily available aryl halide derivatives and phenyl acetylene. The coupling reaction using nickel complex of N,N′-Bis(2-hydroxyethyl)ethylenediami
- Naeimi, Hossein,Kiani, Fatemeh
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- Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters
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Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.
- Ruengsangtongkul, Sureeporn,Chaisan, Nattawadee,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
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supporting information
p. 2514 - 2517
(2019/04/30)
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- Magnetic Cu–Schiff base complex with an ionic tail as a recyclable bifunctional catalyst for base/Pd-free Sonogashira coupling reaction
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Abstract: A Cu(II)–Schiff base complex containing imidazolium ionic phase was prepared and decorated on γ-Fe2O3 magnetic nanoparticles (γ-Fe2O3@Cu(II)IL-SB) and found to be an efficient catalyst for the Pd- and base-free Sonogashira coupling reaction. The heterogeneous catalyst was characterized by FTIR spectroscopy, UV–visible spectroscopy, FE-SEM, TEM, XRD spectroscopy, EDX spectroscopy, VSM, ICP spectroscopy, and atomic absorption spectroscopy. The coupling reactions were performed using the catalyst under mild and base-free conditions, and high-to-excellent yields were obtained for a variety of substrates. The catalyst demonstrates a dual-functionality arising from metal sites and imidazolium moieties and that the later plays a base role. Reusability and stability of γ-Fe2O3@Cu(II)IL-SB were studied several times, which can be reused up to eight consecutive runs with at least reduction in catalytic activity. Also, the mechanism of this bifunctional catalytic system was thoroughly investigated. Graphic abstract: A new and efficient method has been developed for the base- and Pd-free Sonogashira cross-coupling reactions of aryl halides with phenyl acetylene using a bifunctional γ-Fe2O3@Cu(II)IL-SB catalyst with imidazolium moiety under mild conditions[Figure not available: see fulltext.].
- Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali
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p. 2693 - 2705
(2019/07/23)
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- Imidazolium chloride-Co(iii) complex immobilized on Fe3O4@SiO2 as a highly active bifunctional nanocatalyst for the copper-, phosphine-, and base-free Heck and Sonogashira reactions
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A heterogeneous, magnetically recoverable Fe3O4@SiO2@Im[Cl]Co(iii)-melamine nanocomposite was prepared by immobilization of a novel Co(iii) Schiff base complex on Fe3O4@SiO2 nanoparticles followed by treatment with melamine, and was found to be an efficient catalyst for the Heck and Sonogashira reactions. The reactions were performed in the presence of the catalyst (0.5 mol% Co) along with Mn additive in the absence of any base, phosphine ligand, or Cu/co-catalyst in ethanol under reflux conditions. The nanocatalyst was well studied by FTIR, CHN, XRD, XPS, TGA, EDX, VSM, ICP, NMR, FE-SEM, TEM, BET, CV, and DLS analyses. The catalyst was compatible with a variety of substrates, with which all the Heck and Sonogashira coupling products were obtained in high to excellent yields. Also, protocols such as hot filtration, three-phase testing, and mercury poisoning provided a complete insight into the nature of the heterogeneous catalyst. The recycling and reuse of the catalyst were studied for both coupling reactions several times. Moreover, the mechanism of the coupling reactions was entirely investigated.
- Kazemnejadi, Milad,Alavi, Seyyedeh Ameneh G.,Rezazadeh, Zinat,Nasseri, Mohammad Ali,Allahresani, Ali,Esmaeilpour, Mohsen
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p. 1718 - 1734
(2019/04/08)
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- Pd(0) nanoparticles immobilized on multinitrogen functionalized halloysite for promoting Sonogashira reaction: studying the role of the number of surface nitrogens in catalytic performance
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Halloysite nanoclay, Hal, was amine-functionalized and subsequently reacted with 2,4,6-trichloro-1,3,5-triazine, TCT, and ethylenediamine, EDA, to provide multinitrogen containing functionality on the surface of Hal. The resulting surface-modified Hal, Ha
- Sadjadi, Samahe,Heravi, Majid M.,Masoumi, Baharak,Kazemi, Shaghayegh Sadat
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p. 119 - 134
(2019/01/30)
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- Enhanced catalytic activity of CuI/diethoxyphosphoryl-1,10-phenanthrolines in ‘on water’ Cu-catalyzed Sonogashira reaction
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The use of CuI/diethoxyphosphoryl-1,10-phenanthrolines and ‘on water’ conditions in the Cu-catalyzed Sonogashira reaction of aryl iodides with terminal alkynes significantly increases the reaction rate as compared to that in organic solvents.
- Mitrofanov, Alexander Yu.,Beletskaya, Irina P.
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p. 378 - 379
(2019/08/16)
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