Cobalt-Catalyzed Directed Alkylation of Olefinic C-H Bond with Primary and Secondary Alkyl Chlorides

被引:14
作者
Yamakawa, Takeshi [1 ]
Seto, Yuan Wah [1 ]
Yoshikai, Naohiko [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
基金
新加坡国家研究基金会;
关键词
cobalt; C-H activation; alkylations; alkyl halides; alkenes; CROSS-COUPLING REACTIONS; ARYL GRIGNARD-REAGENTS; AROMATIC IMINES; HALIDES; IRON; ACTIVATION; CARBOXAMIDES; ARENES; FUNCTIONALIZATIONS; HYDROARYLATION;
D O I
10.1055/s-0034-1379247
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cobalt-N -heterocyclic carbene catalytic system promotes pyridine-directed olefinic C-H alkylation reactions using a variety of primary and secondary alkyl chlorides under mild conditions. Radical clock experiments suggest that the reaction involves single-electron transfer from the cobalt intermediate to the alkyl chloride
引用
收藏
页码:340 / 344
页数:5
相关论文
共 39 条
[1]   Ruthenium(IV) alkylidenes as precatalysts for direct arylations of Alkenes with aryl chlorides and an application to sequential catalysis [J].
Ackermann, Lutz ;
Born, Robert ;
Alvarez-Bercedo, Paula .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (33) :6364-6367
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877
[4]   Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].
Ackermann, Lutz ;
Novak, Petr ;
Vicente, Ruben ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048
[5]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[6]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]
[7]   Cobalt-Catalyzed Cross-Coupling Reactions [J].
Cahiez, Gerard ;
Moyeux, Alban .
CHEMICAL REVIEWS, 2010, 110 (03) :1435-1462
[8]   A New Efficient Catalytic System for the Chemoselective Cobalt-Catalyzed Cross-Coupling of Aryl Grignard Reagents with Primary and Secondary Alkyl Bromides [J].
Cahiez, Gerard ;
Chaboche, Christophe ;
Duplais, Christophe ;
Moyeux, Alban .
ORGANIC LETTERS, 2009, 11 (02) :277-280
[9]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[10]   A Unified Strategy for Iron-Catalyzed ortho-Alkylation of Carboxamides [J].
Fruchey, Erin R. ;
Monks, Brendan M. ;
Cook, Silas P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) :13130-13133