Copper-Catalyzed Dehydrogenative Cross-Coupling of Benzothiazoles with Thiazoles and Polyfluoroarene

被引:99
作者
Fan, Shilu [1 ]
Chen, Zhao [2 ]
Zhang, Xingang [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] SW Petr Univ, Sch Chem & Chem Engn, Chengdu 610500, Sichuan, Peoples R China
关键词
C-H FUNCTIONALIZATION; ELECTRON-DEFICIENT POLYFLUOROARENES; BOND FORMATION; DIRECT ARYLATION; GENERAL-METHOD; SIMPLE ARENES; INDOLES; ACTIVATION; EFFICIENT; AZOLES;
D O I
10.1021/ol3023165
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarene under mild reaction conditions is described. This protocol provides a straightforward and operationally simple method for the synthesis of the 2,2'-linkage of thiazoles and 2-polyfluoroarylthiazoles of interest in life and material sciences.
引用
收藏
页码:4950 / 4953
页数:4
相关论文
共 81 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]   C-F Bond Activation in Organic Synthesis [J].
Amii, Hideki ;
Uneyama, Kenji .
CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183
[4]   Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom [J].
Babudri, Francesco ;
Farinola, Gianluca M. ;
Naso, Francesco ;
Ragni, Roberta .
CHEMICAL COMMUNICATIONS, 2007, (10) :1003-1022
[5]   Thiopeptide antibiotics [J].
Bagley, MC ;
Dale, JW ;
Merritt, EA ;
Xiong, A .
CHEMICAL REVIEWS, 2005, 105 (02) :685-714
[6]   Copper-mediated C-H bond arylation of arenes with arylboronic acids [J].
Ban, Ikuya ;
Sudo, Tomoko ;
Taniguchi, Tadashi ;
Itami, Kenichiro .
ORGANIC LETTERS, 2008, 10 (16) :3607-3609
[7]   Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].
Bernini, Roberta ;
Fabrizi, Giancarlo ;
Sferrazza, Alessio ;
Cacchi, Sandro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081
[8]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210
[9]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[10]   A facile, metal- and solvent-free, autoxidative coupling of quinolines with indoles and pyrroles [J].
Brasse, Mikael ;
Ellman, Jonathan A. ;
Bergman, Robert G. .
CHEMICAL COMMUNICATIONS, 2011, 47 (17) :5019-5021