Copper-Catalyzed Direct Alkynylation of Electron-Deficient Polyfluoroarenes with Terminal Alkynes Using O2 as an Oxidant

被引:232
作者
Wei, Ye [1 ]
Zhao, Huaiqing [1 ]
Kan, Jian [1 ]
Su, Weiping [1 ]
Hong, Maochun [1 ]
机构
[1] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China
关键词
C-H BOND; GACL3-CATALYZED ORTHO-ETHYNYLATION; INTERMOLECULAR DIRECT ARYLATION; REDUCTIVE ELIMINATION; COUPLING REACTIONS; ROOM-TEMPERATURE; FUNCTIONALIZATION; ALKENYLATION; ACTIVATION; CARBON;
D O I
10.1021/ja910461e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-catalyzed direct alkynylation of electron-deficient polyfluoroarenes with a wide range of terminal alkynes is realized for the first time. The reaction proceeds under mild conditions with O-2 as an oxidant.
引用
收藏
页码:2522 / +
页数:3
相关论文
共 52 条
[1]  
Albéniz AC, 2001, CHEM-EUR J, V7, P2481, DOI 10.1002/1521-3765(20010601)7:11<2481::AID-CHEM24810>3.3.CO
[2]  
2-U
[3]   GaCl3-catalyzed ortho-ethynylation reaction of N-benzylanilines [J].
Amemiya, R ;
Fujii, A ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2004, 45 (22) :4333-4335
[4]   Copper as a Powerful Catalyst in the Direct Alkynylation of Azoles [J].
Besselievre, Francois ;
Piguel, Sandrine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (50) :9553-9556
[5]   POLYACETYLENVERBINDUNGEN .52. UBER DEN MECHANISMUS DER OXYDATIVEN DIMERISIERUNG VON ACETYLENVERBINDUNGEN [J].
BOHLMANN, F ;
SCHONOWSKY, H ;
GRAU, G ;
INHOFFEN, E .
CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (03) :794-&
[6]   Direct Alkynylation of Indole and Pyrrole Heterocycles [J].
Brand, Jonathan P. ;
Charpentier, Julie ;
Waser, Jerome .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349
[7]   DOPED GLASSY-CARBON MATERIALS (DGC) - LOW-TEMPERATURE SYNTHESIS, STRUCTURE, AND CATALYTIC BEHAVIOR [J].
CALLSTROM, MR ;
NEENAN, TX ;
MCCREERY, RL ;
ALSMEYER, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4954-4956
[8]  
Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
[9]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115
[10]   Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway [J].
Chernyak, Natalia ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5636-+