Pyridine N-Oxides as Ligands in Cu-Catalyzed N-Arylation of Imidazoles in Water

被引：138
作者：
Liang, Lei [1 ]
Li, Zhengkai [1 ]
Zhou, Xiangge [1 ,2 ]
机构：
[1] Sichuan Univ, Coll Chem, Inst Homogeneous Catalysis, Chengdu 610064, Peoples R China
[2] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing 210093, Peoples R China
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 15期
关键词：
CROSS-COUPLING REACTIONS; AQUEOUS-MEDIA; ARYL HALIDES; NITROGEN NUCLEOPHILES; ORGANIC-REACTIONS; HIGHLY EFFICIENT; COPPER-CATALYST; O-ARYLATION; AMINATION; BROMIDES;
D O I：
10.1021/ol9010773
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Arylation of imidazoles with aryl halides catalyzed by a combination of copper(II) sulfate and 1,2-bis(2-pyridyl)-ethane-N'N'-dioxide in water afforded up to 95% yield.
引用
收藏
页码：3294 / 3297
页数：4
相关论文
共 67 条
[1]   Roles of water for chemical reactions in high-temperature water [J].
Akiya, N ;
Savage, PE .
CHEMICAL REVIEWS, 2002, 102 (08) :2725-2750
[2]  
ALBINI A, 1993, SYNTHESIS-STUTTGART, P263
[3]   Copper-catalyzed N-arylation of imidazoles and benzimidazoles [J].
Altman, Ryan A. ;
Koval, Erica D. ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6190-6199
[4]   4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2006, 8 (13) :2779-2782
[5]   The copper-catalyzed N-arylation of indoles [J].
Antilla, JC ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688
[6]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[7]   Low-pressure solubility of carbon dioxide in room-temperature ionic liquids measured with a quartz crystal microbalance [J].
Baltus, RE ;
Culbertson, BH ;
Dai, S ;
Luo, HM ;
DePaoli, DW .
JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (02) :721-727
[8]   Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides:: a straightforward approach to benzo[d]oxazoles in water [J].
Barbero, Nekane ;
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther .
TETRAHEDRON, 2007, 63 (42) :10425-10432
[9]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[10]  
Blackmond D.G., 2007, ANGEW CHEM, V119, P3872
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