135-70-6Relevant articles and documents
Polyamine anchored palladium catalyst for suzuki-miyaura and one-pot O-alkylation-suzuki reactions
Patel, Krupa N.,Bedekar, Ashutosh V.
, p. 1710 - 1717 (2015)
Polymer anchored amine-palladium complexes were screened as catalysts for Suzuki-Miyaura coupling reactions of aryl halides. The robust, recyclable catalyst was effective in this reaction of aryl bromides and iodides. Aryl bromide was found to undergo selective Suzuki-Miyaura reaction with phenyl boronic acid, even in presence of styrene. The catalyst system was further employed for one-pot O-alkylation-Suzuki reaction to prepare alkoxy biaryl systems in good conversions.
Regioselective α-arylation of N-vinylpyrroles by the Heck reaction
Shmidt, A. F.,Vladimirova, T. A.,Shmidt, E. Yu.,Dmitrieva, T. V.
, p. 767 - 768 (1995)
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Microwave-assisted Suzuki coupling on a KF-alumina surface: Synthesis of polyaryls
Basu, Basudeb,Das, Pralay,Bhuiyan, Md. Mosharef H.,Jha, Satadru
, p. 3817 - 3820 (2003)
A range of conjugated polyaryls has been synthesized through one-pot microwave assisted palladium-catalyzed consecutive Suzuki coupling reactions on a KF-alumina surface with notable features including rapid reaction times, solvent-free conditions, high yields, atom economic and air-insensitive reactions.
Stable ferrocenyl-NHC Pd(II) complexes: Evidence of C-H ?H/π interaction and M-O bonding in solution
Azpiroz, Ramón,Sharma, Pankaj,Javier Pérez-Flores,Gutierrez, René,Espinosa-Pérez, Georgina,Lara-Ochoa, Francisco
, p. 196 - 206 (2017)
New air stable palladium(II)-NHC complexes where carbene ligand is substituted with a bulky ferrocenylmethyl and pyranylmethyl groups viz. PdI(Phpy){FcCH2-C3H2N2-Me} (3), PdI2{FcCH2-C3H2N2-C6H11O} (4) and PdI2{FcCH2-NHC}(L) (5–10) (NHC = C3H2N2-Me or C6H11O; L = pyridine, imidazole and thiazole) are reported. The presence of C-H?H/π interactions has been confirmed for complex 3 by NOE interaction and multinuclear NMR experiments. In addition, for this complex, a quantum chemical analysis was performed using PM3 semi-empirical calculations to find the possible conformers. The conformation with minimal energy confirms the NMR interpretation for complex 3. The M-O bond in complex 4 was ruptured by the reaction of an extra pyridine ligand to afford PdI2{FcCH2-C3H2N2-C6H11O}(py) (5) which was synthetized differently by reacting NHC ligand, Pd(OAc)2 and pyridine. Molecular structure of complex 5 was determined by X-ray diffraction. The catalytic activity of these complexes was checked in Suzuki-Miyaura reaction. Complex 5 exhibits excellent conversions and selectivities (up to 99%).
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Bergmann,Weizmann
, p. 415,417 (1944)
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Bamfield,Quan
, p. 537 (1978)
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Mayo,Hurwitz
, p. 776 (1949)
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McKillop,A. et al.
, p. 4041 - 4050 (1970)
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N-Heterocyclic Carbene–Palladium Complex onto Graphene Oxide and Poly (ethylene glycol) (PEG) Applied as Superior Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water
Heravi, Majid M.,Asadi, Shima,Hoseini Chopani, Seyede Mahdiye,Jaderi, Elham
, (2020)
Using polymeric nanocomposites incorporated Pd to promote C-C coupling reactions has been found as one of the most successful strategies. In this paper we apply graphene oxide (GO) as an efficient surface immobilized by water-soluble poly (ethylene glycol)-imidazole followed by introduction of PdCl2 salt to obtain the desired catalyst. Catalytic performance of this composite was investigated in the Suzuki–Miyaura cross-coupling reaction under mild reaction conditions and superior results were obtained. The hydrophilic nature of the catalyst and well distribution of Pd lead to superior catalytic activity in water media. Moreover, the Suzuki–Miyaura reaction proceed successfully with excellent yield and short reaction time without any loss of activity even after seven consecutive reaction cycles.
Homocoupling of arylboronic acids and potassium aryltrifluoroborates catalyzed by protein-stabilized palladium nanoparticles under air in water
Prastaro, Alessandro,Ceci, Pierpaolo,Chiancone, Emilia,Boffi, Alberto,Fabrizi, Giancarlo,Cacchi, Sandro
, p. 2550 - 2552 (2010)
Palladium nanoparticles stabilized primarily within the protein cavity of a highly thermostable Dps protein (DNA binding protein from starved cells) from the thermophilic bacterium Thermosynechoccus elongatus provide an efficient catalyst for the homocoupling of boronic acids and potassium aryltrifluoroborates in water under aerobic phosphine-free conditions. Symmetrical biaryls have been isolated in good to excellent yields. Potassium aryltrifluoroborates give similar or better results than the corresponding arylboronic acids.
Pd-catalyzed desulfonylative homocoupling of arenesulfonyl chlorides in the presence of hexamethyldisilane forming biaryls
Kashiwabara, Taigo,Tanaka, Masato
, p. 7125 - 7128 (2005)
Arenesulfonyl chlorides undergo desulfonylative homo-coupling upon heating with hexamethyldisilane in the presence of Pd2(dibenzylideneacetone) 3?CHCl3 as a precatalyst to afford biaryls. Diaryl sulfides are occasionally formed as byproducts.
Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles
Bao, Yan-Sai,Cui, Xin-Yu,Han, Zheng-Bo,Li, Xin,Tang, Hong,Yang, Ming,Zhang, Yu-Yang,Zhao, Kun,Zhou, Mei-Li
, (2020/12/17)
Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.
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
Liu, Qingxiang,Zhang, Xiantao,Zhao, Zhixiang,Li, Xinying,Zhang, Wei
supporting information, p. 605 - 613 (2021/02/01)
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.
