CuI/PPh3 catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes in water in the absence of palladium

被引:54
作者
Guan, Jin Tao [1 ]
Yu, Guang-Ao [1 ]
Chen, Lei [1 ]
Weng, Tan Qing [1 ]
Yuan, Jing Jing [1 ]
Liu, Sheng Hua [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China
基金
中国国家自然科学基金;
关键词
water; copper(I) iodide; aryl iodide; terminal alkyne; Sonogashira coupling reaction; LIGAND-FREE; CONJUGATED ENYNES; ORGANIC-CHEMISTRY; SUZUKI-MIYAURA; VINYL IODIDES; COPPER; HALIDES; DERIVATIVES; ACETYLENES; 1-ALKYNES;
D O I
10.1002/aoc.1474
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The Sonogashira cross-coupling of aryl iodides with terminal alkynes catalyzed by a simple and inexpensive catalyst CuI/PPh3 in water as the sole solvent has been reported. In the presence of CuI/PPh3, with KOH used as a base, a number of aryl iodides were treated with alkynes to afford the corresponding products in moderate to excellent yields. Copyright (c) 2008 John Wiley & Sons, Ltd.
引用
收藏
页码:75 / 77
页数:3
相关论文
共 42 条
[1]   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
[2]  
[Anonymous], 2004, Metal-Catalyzed Cross-Coupling Reactions
[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]   The nickel-catalyzed Sonogashira-Hagihara reaction [J].
Beletskaya, IP ;
Latyshev, GV ;
Tsvetkov, AV ;
Lukashev, NV .
TETRAHEDRON LETTERS, 2003, 44 (27) :5011-5013
[5]   Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions [J].
Biffis, Andrea ;
Scattolin, Elena ;
Ravasio, Nicoletta ;
Zaccheria, Federica .
TETRAHEDRON LETTERS, 2007, 48 (49) :8761-8764
[6]   Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].
Bunz, UHF .
CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644
[7]   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
[8]   Palladium-free copper-catalyzed coupling reaction of aryl iodides and terminal acetylenes in water [J].
Chen, Gong ;
Zhu, Xinhai ;
Cai, Jiwen ;
Wan, Yiqian .
SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) :1355-1361
[9]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[10]  
Cornils B., 1998, Aqueous-Phase Organometallic Catalysis