Efficient C-S cross coupling catalyzed by Cu2O

被引：101

作者：

Xu, Hua-Jian ^{[2
]}

Zhao, Xiao-Yang ^{[2
]}

Deng, Jin ^{[1
]}

Fu, Yao ^{[1
]}

Feng, Yi-Si ^{[2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[2] Hefei Univ Technol, Sch Chem Engn, Hefei 230009, Peoples R China

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 04期

基金：

中国国家自然科学基金;

关键词：

SULFUR BOND FORMATION; ALPHA-AMINO-ACIDS; ARYL HALIDES; BORONIC ACIDS; THIOLS; COPPER; IODIDES; LIGAND; ARYLATION; THIOETHERS;

D O I：

10.1016/j.tetlet.2008.11.029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A protocol for the copper-catalyzed C-S bond formation between aryl, alkyl, or heteroaryl thiols and aryl or heteroaryl halides is reported. The reaction is catalyzed by Cu2O which shows the highest catalytic activity with ethyl 2-oxocyclohexanecarboxylate ligand in DMSO at 80 degrees C. The corresponding coupling products are obtained with good to excellent yields under relatively mild reaction conditions with good chemoselectivity and functional group tolerance. (c) 2008 Published by Elsevier Ltd.

引用

页码：434 / 437

页数：4

共 36 条

[1] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[2] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].

Bates, CG ;

Gujadhur, RK ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (16) :2803-2806

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

Beletskaya, IP ;

Cheprakov, AV .

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

[4] Simple and efficient recyclable catalytic system for performing copper-catalysed S-arylation reactions in the presence of water [J].

Carril, Monica ;

SanMartin, Raul ;

Dominguez, Esther ;

Tellitu, Imanol .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (18) :5100-5105

[5] 1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols [J].

Chen, Yao-Jung ;

Chen, Hsin-Hung .

ORGANIC LETTERS, 2006, 8 (24) :5609-5612

[6] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[7] Iron-catalyzed S-arylation of thiols with aryl iodides [J].

Correa, Arkaitz ;

Carril, Monica ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) :2880-2883

[8] CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands [J].

Deng, W ;

Zou, Y ;

Wang, YF ;

Liu, L ;

Guo, QX .

SYNLETT, 2004, (07) :1254-1258

[9]

Deng W, 2004, CHINESE J ORG CHEM, V24, P150

[10] A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols [J].

Fernández-Rodríguez, MA ;

Shen, QL ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2180-2181

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