Direct Amination of Azoles via Catalytic C-H, N-H Coupling

被引:347
作者
Monguchi, Daiki [1 ]
Fujiwara, Taiki [1 ]
Furukawa, Hirotoshi [1 ]
Mori, Atsunori [1 ]
机构
[1] Kobe Univ, Dept Sci & Chem Engn, Kobe, Hyogo 6578501, Japan
关键词
BOND FORMATION; DIRECT ARYLATION; ARYL HALIDES; EFFICIENT; FUNCTIONALIZATION; 2,5-DIARYLTHIAZOLE; BROMOTHIOPHENE; DERIVATIVES; AMIDATION; ACTIVATOR;
D O I
10.1021/ol900298e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
C-H, N-H Coupling of azoles takes place with several amines in the presence of a copper catalyst to undergo amination at the 2-position. The reaction of benzothiazole with N-methylaniline in the presence of sodium acetate and 20 mol % Cu(OAc)(2) in xylene under an oxygen atmosphere afforded the aminated product in 81% yield.
引用
收藏
页码:1607 / 1610
页数:4
相关论文
共 60 条
[11]   An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].
Collman, JP ;
Zhong, M .
ORGANIC LETTERS, 2000, 2 (09) :1233-1236
[12]   A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds [J].
Do, Hien-Ouang ;
Khan, Rana M. Kashif ;
Daugulis, Olafs .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :15185-15192
[13]   C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].
Dwight, Timothy A. ;
Rue, Nicholas R. ;
Charyk, Dagmara ;
Josselyn, Ryan ;
DeBoef, Brenton .
ORGANIC LETTERS, 2007, 9 (16) :3137-3139
[14]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[15]  
2-6
[16]   Expanding the scope of C-H amination through catalyst design [J].
Espino, CG ;
Fiori, KW ;
Kim, M ;
Du Bois, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15378-15379
[17]   Catalytic intermolecular amination of C-H bonds: Method development and mechanistic insights [J].
Fiori, Kristin Williams ;
Du Bois, J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (03) :562-568
[18]   syn-1,2-amino alcohols via diastereoselective allylic C-H amination [J].
Fraunhoffer, Kenneth J. ;
White, M. Christina .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (23) :7274-+
[19]  
FURUKAWA H, 2009, HETEROCYCLE IN PRESS
[20]   Activated aryl chlorides: Useful partners for the coupling with 2-substituted thiazoles in the palladium-catalysed C-H activation/functionalisation reaction [J].
Gottumukkala, Aditya L. ;
Doucet, Henri .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, (23) :3629-3632