Ligand-Free Copper-Catalyzed Amination of Heteroaryl Halides with Alkyl- and Arylamines

被引:33
作者
Liu, Zhen-Jiang [2 ]
Vors, Jean-Pierre [3 ]
Gesing, Ernst R. F. [1 ]
Bolm, Carsten [2 ]
机构
[1] Bayer CropSci AG, BCS R I CI, D-40789 Monheim, Germany
[2] Rhein Westfal TH Aachen, Inst Organ Chem, D-52056 Aachen, Germany
[3] Bayer CropSci SAS, Ctr Rech La Dagoire, F-69009 Lyon, France
关键词
aminopyridines; aminopyrimidines; copper; N-heteroarylation; ligand-free conditions; LONG-LIVED CATALYSTS; C-N; ARYL HALIDES; INTRAMOLECULAR AMINATION; PALLADIUM; ARYLATION; EFFICIENT; SELECTIVITY; BROMIDES; MILD;
D O I
10.1002/adsc.201000708
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
N-Heteroarylations of alkyl- and aryl-amines with various heteroaryl halides have been achieved by ligand-free copper-catalyzed cross-couplings affording aminopyridines and aminopyrimidines in moderate to high yields (up to 99% yield).
引用
收藏
页码:3158 / 3162
页数:5
相关论文
共 61 条
[1]  
Anderson K.W., 2006, ANGEW CHEM, V118, P6673, DOI [DOI 10.1002/ANGE.200601612, 10.1002/ange.200601612]
[2]   Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].
Anderson, Kevin W. ;
Tundel, Rachel E. ;
Ikawa, Takashi ;
Altman, Ryan A. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527
[3]  
[Anonymous], 1996, COMPREHENSIVE HETERO, DOI DOI 10.1016/B978-008096518-5.00109-X
[4]   6-amino-2,2'-bipyridine as a new fluorescent organic compound [J].
Araki, K ;
Mutai, T ;
Shigemitsu, Y ;
Yamada, M ;
Nakajima, T ;
Kuroda, S ;
Shimao, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (04) :613-617
[5]  
Arndt K. E., 1996, Patent, Patent No. [WO 9601828, 9601828, WO 96/01828]
[6]   Catalytic amination of 5-iodouracil derivatives [J].
Arterburn, JB ;
Pannala, M ;
Gonzalez, AM .
TETRAHEDRON LETTERS, 2001, 42 (08) :1475-1477
[7]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[8]   Transition metal-free amination of aryl halides-A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines [J].
Bolliger, Jeanne L. ;
Frech, Christian M. .
TETRAHEDRON, 2009, 65 (06) :1180-1187
[9]   Palladium and copper-catalysed arylation reactions in the presence of water, with a focus on carbon-heteroatom bond formation [J].
Carril, Monica ;
SanMartin, Raul ;
Dominguez, Esther .
CHEMICAL SOCIETY REVIEWS, 2008, 37 (04) :639-647
[10]   Efficient nucleophilic substitution reactions of pyrimidyl and pyrazyl halides with nucleophiles, under focused microwave irradiation [J].
Cherng, YH .
TETRAHEDRON, 2002, 58 (05) :887-890