Nickel-Catalyzed Cross-Coupling of Aryl Fluorides and Organozinc Reagents

被引:65
作者
Zhu, Feng
Wang, Zhong-Xia [1 ]
机构
[1] Univ Sci & Technol China, CAS Key Lab Soft Matter Chem, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
C-F ACTIVATION; GRIGNARD-REAGENTS; BOND FORMATION; ALKYL FLUORIDES; HALIDES; CHLORIDES; SUBSTITUTION; EXPLORATION; COMPLEXES; MECHANISM;
D O I
10.1021/jo500619f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ni(PCy3)(2)Cl-2 was demonstrated to effectively catalyze cross-coupling of aryl fluorides and organozinc reagents. Both electron-poor and -rich aryl fluorides Can react effectively with nucleophiles including aryl-, methyl-, and benzylzinc chlorides. A wide range of substituents and functional groups are tolerated. In the presence of a directing group, PhC(O), the reaction is selective for cleavage of the C-F bond ortho to the carbonyl substituent in a difluoroarene.
引用
收藏
页码:4285 / 4292
页数:8
相关论文
共 79 条
[1]   Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides [J].
Ackermann, L ;
Born, R ;
Spatz, JH ;
Meyer, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) :7216-7219
[2]   Kumada-Corriu Cross-Couplings with 2-Pyridyl Grignard Reagents [J].
Ackermann, Lutz ;
Potukuchi, Harish K. ;
Kapdi, Anant R. ;
Schulzke, Carola .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (11) :3300-3303
[3]   C-F Bond Activation in Organic Synthesis [J].
Amii, Hideki ;
Uneyama, Kenji .
CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183
[4]   Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides [J].
Andrei, D ;
Wnuk, SF .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :405-408
[5]  
[Anonymous], METAL CATALYZED CROS
[6]   Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides:: p-orientation in the polyarylthiolation of polyfluorobenzenes [J].
Arisawa, Mieko ;
Suzuki, Takaaki ;
Ishikawa, Tomofumi ;
Yamaguchi, Masahiko .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12214-+
[7]   Proximity effects in the palladium-catalyzed substitution of aryl fluorides [J].
Bahmanyar, S ;
Borer, BC ;
Kim, YM ;
Kurtz, DM ;
Yu, S .
ORGANIC LETTERS, 2005, 7 (06) :1011-1014
[8]   THE REACTION OF BENZYLMAGNESIUM CHLORIDE AND DIBENZYLMAGNESIUM WITH PYRIDINE [J].
BENKESER, RA ;
HOLTON, DS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (12) :5861-5862
[9]  
Bernard B., 1980, SYNTHESIS-STUTTGART, V11, P926
[10]  
Böhm VPW, 2001, ANGEW CHEM INT EDIT, V40, P3387