Highly efficient copper(0)-catalyzed Suzuki-Miyaura cross-coupling reactions in reusable PEG-400

被引：148

作者：

Mao, Jincheng ^{[1
]}

Guo, Jun ^{[1
]}

Fang, Fubing ^{[1
]}

Ji, Shun-Jun ^{[1
]}

机构：

[1] Suzhou Univ, Coll Chem & Chem Engn, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

TETRAHEDRON | 2008年 / 64卷 / 18期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tet.2008.02.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Readily available copper powder with K2CO3 as the base was extremely effective catalyst for Suzuki-Miyaura coupling reaction performed in PEG-400, which afforded almost quantitative coupling products of aryl iodides. Using iodine as additive, coupling products of aryl bromides or chlorides could be obtained with moderate to good yields. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3905 / 3911

页数：7

共 66 条

[1] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201

[2] An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693

[3] Homogeneous catalysts supported on soluble polymers: Biphasic Suzuki-Miyaura coupling of aryl chlorides using phase-tagged palladium-phosphine catalysts [J].

an der Heiden, M ;

Plenio, H .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (07) :1789-1797

[4] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].

Anderson, KW ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177

[5] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[6] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[7]

CAI J, 2004, ORG LETT, V4, P4723

[8]

Collman J.P., 1987, PRINCIPLES APPL ORGA

[9] Gas-phase cyclisation reactions of 1-(2-arylthiophenyl)alkaniminyl and 2-(aryliminomethyl)thiophenoxyl radicals [J].

Creed, T ;

Leardini, R ;

McNab, H ;

Nanni, D ;

Nicolson, IS ;

Reed, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (09) :1079-1085

[10] Synthesis of a novel C2-symmetric thiourea and its application in the Pd-catalyzed cross-coupling reactions with arenediazonium salts under aerobic conditions [J].

Dai, MJ ;

Liang, B ;

Wang, CH ;

Chen, JH ;

Yang, Z .

ORGANIC LETTERS, 2004, 6 (02) :221-224

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