Cu(OAc)2 catalyzed Sonogashira cross-coupling reaction in amines

被引:25
作者
Guo, Sheng Mei [1 ]
Deng, Chen Liang [1 ]
Li, Jin Heng [1 ]
机构
[1] Hunan Normal Univ, Coll Chem & Chem Engn, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Peoples R China
基金
中国国家自然科学基金;
关键词
Cu(OAc)(2); Sonogashira cross-coupling reaction; aryl halide; alkyne;
D O I
10.1016/j.cclet.2006.11.019
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple Cu(OAc)(2) catalyzed Sonogashira coupling protocol is presented. It was found that the couplings of a variety of aryl halides with terminal alkynes were conducted smoothly to afford the corresponding desired products in moderate to excellent yields, using Cu(OAc)(2) as the catalyst and Et3N as the solvent. (c) 2006 Jin Heng Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:13 / 16
页数:4
相关论文
共 33 条
[1]   Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones [J].
Adjabeng, G ;
Brenstrum, T ;
Frampton, CS ;
Robertson, AJ ;
Hillhouse, J ;
McNulty, J ;
Capretta, A .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :5082-5086
[2]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[3]   A copper- and amine-free Sonogashira coupling reaction promoted by a ferrocene-based phosphinimine-phosphine ligand at low catalyst loading [J].
Arques, A ;
Auñon, D ;
Molina, P .
TETRAHEDRON LETTERS, 2004, 45 (22) :4337-4340
[4]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[5]  
Bohlmann F, 1973, NATURALLY OCCURRING
[6]   2-aryl and 2-heteroaryl indoles from 1-alkynes and o-lodotrifluoroacetanilide through a domino copper-catalyzed coupling-cyclization process [J].
Cacchi, S ;
Fabrizi, G ;
Parisi, LM .
ORGANIC LETTERS, 2003, 5 (21) :3843-3846
[7]   SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES [J].
CASSAR, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :253-257
[8]   A copper- and amine-free sonogashira reaction employing aminophosphines as ligands [J].
Cheng, J ;
Sun, YH ;
Wang, F ;
Guo, MJ ;
Xu, JH ;
Pan, Y ;
Zhang, ZG .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) :5428-5432
[9]   A copper-free Sonogashira reaction using a Pd/MgLa mixed oxide [J].
Cwik, A ;
Hell, Z ;
Figueras, F .
TETRAHEDRON LETTERS, 2006, 47 (18) :3023-3026
[10]   PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES [J].
DIECK, HA ;
HECK, FR .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :259-263