Aryl halide tolerated electrophilic amination of arylboronic acids with N-chloroamides catalyzed by CuCl at room temperature

被引:118
作者
He, Chuan [1 ]
Chen, Chong [1 ]
Cheng, Jin [1 ]
Liu, Chao [1 ]
Liu, Wei [1 ]
Li, Qiang [1 ]
Lei, Aiwen [1 ]
机构
[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
amides; amination; copper; cross-coupling; homogeneous catalysis;
D O I
10.1002/anie.200801427
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) N-Cl is no competition: Aryl halides were tolerated in an efficient ligandless CuCl-catalyzed electrophilic amination reaction of arylboronic acids with N-chloroamides (see scheme; Ac=acetoxy). This coupling proceeded smoothly at ambient temperature, and products were obtained with good to excellent yields. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6414 / 6417
页数:4
相关论文
共 58 条
[1]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[2]   Rhodium-catalyzed Beckmann rearrangement [J].
Arisawa, M ;
Yamaguchi, M .
ORGANIC LETTERS, 2001, 3 (02) :311-312
[3]  
Armesto XL, 1998, CHEM SOC REV, V27, P453, DOI 10.1039/a827453z
[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]   Recent synthetic advances in the nucleophilic amination of benzenes [J].
Belfield, AJ ;
Brown, GR ;
Foubister, AJ .
TETRAHEDRON, 1999, 55 (38) :11399-11428
[6]   Copper-catalyzed electrophilic amination of organozinc nucleophiles:: Documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons [J].
Berman, AM ;
Johnson, JS .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :219-224
[7]   Nickel-catalyzed electrophilic amination of organozinc halides [J].
Berman, AM ;
Johnson, JS .
SYNLETT, 2005, (11) :1799-1801
[8]   Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents [J].
Berman, AM ;
Johnson, JS .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :364-366
[9]   Copper-catalyzed electrophilic amination of diorganozinc reagents [J].
Berman, AM ;
Johnson, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5680-5681
[10]   Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol [J].
Campbell, Matthew J. ;
Johnson, Jeffrey S. .
ORGANIC LETTERS, 2007, 9 (08) :1521-1524