CuBr/rac-BINOL-catalyzed Sonogashira reaction of terminal alkynes with aryl halides or arylboronic acids

被引：53

作者：

Mao, Jincheng ^{[1
]}

Guo, Jun ^{[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：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2008年 / 284卷 / 1-2期

基金：

中国博士后科学基金;

关键词：

Sonogashira coupling reaction; aryl halides; terminal alkynes; arylboronic acid; low cost;

D O I：

10.1016/j.molcata.2008.01.006

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

CuBr/rac-BINOL-catalyzed Sonogashira coupling reaction of aryl halides with terminal alkynes was conducted smoothly to afford the corresponding products with moderate to good yields. We found that the inexpensive catalytic system was also suitable for the coupling reaction of arylboronic acids with terminal alkynes. (C) 2008 Elsevier B.V. All rights reserved.

引用

收藏

页码：85 / 88

页数：4

相关论文

共 21 条

[1] Copper-catalyzed coupling of arylboronic acids and amines [J].

Antilla, JC ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (13) :2077-2079

[2] Design and evolution of copper apatite catalysts for N-arylation of heterocycles with chloro- and fluoroarenes [J].

Choudary, BM ;

Sridhar, C ;

Kantam, ML ;

Venkanna, GT ;

Sreedhar, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9948-9949

[3]

Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222

[4] The first applications of carbene ligands in cross-couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides [J].

Eckhardt, M ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13642-13643

[5] Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts [J].

Gujadhur, RK ;

Bates, CG ;

Venkataraman, D .

ORGANIC LETTERS, 2001, 3 (26) :4315-4317

[6]

Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO

[7]

2-Y

[8] The vinylation of aryl and vinyl halides catalyzed by copper salts [J].

Iyer, S ;

Ramesh, C ;

Sarkar, A ;

Wadgaonkar, PP .

TETRAHEDRON LETTERS, 1997, 38 (46) :8113-8116

[9] CuBr/rac-BINOL-catalyzed N-arylations of aliphatic amines at room temperature [J].

Jiang, Deshou ;

Fu, Hua ;

jiang, Yuyang ;

Zhao, Yufen .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (02) :672-674

[10] Synthesis and biological activity of high-affinity retinoic acid receptor antagonists [J].

Johnson, AT ;

Wang, LM ;

Standeven, AM ;

Escobar, M ;

Chandraratna, RAS .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (07) :1321-1338