Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds

被引:86
作者
Borduas, Nadine [1 ]
Powell, David A. [1 ]
机构
[1] Merck Frosst Ctr Therapeut Res, Kirkland, PQ H9H 3L1, Canada
关键词
D O I
10.1021/jo801322p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds is described. The reaction utilizes an inexpensive copper catalyst - oxidant system that is suitable for the coupling of a range of benzylic C-H bonds with various 1,3-dicarbonyl compounds. Kinetic isotope studies support a mechanism involving a benzylic hydrogen abstraction.
引用
收藏
页码:7822 / 7825
页数:4
相关论文
共 69 条
[1]   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
[2]   Copper catalyzed allylic oxidation with peresters [J].
Andrus, MB ;
Lashley, JC .
TETRAHEDRON, 2002, 58 (05) :845-866
[3]   Intermolecular oxidative enolate heterocoupling [J].
Baran, Phil S. ;
DeMartino, Michael P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :7083-7086
[4]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[5]   Copper catalyzed oxidative alkylation of sp3 C-H bond adjacent to a nitrogen atom using molecular oxygen in water [J].
Basle, Olivier ;
Li, Chao-Jun .
GREEN CHEMISTRY, 2007, 9 (10) :1047-1050
[6]   The palladium-catalyzed C-H activation of benzylic gem-dialkyl groups [J].
Baudoin, O ;
Herrbach, A ;
Guéritte, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5736-5740
[7]   Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].
Campeau, LC ;
Fagnou, K .
CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264
[8]   Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].
Campeau, Louis-Charles ;
Schipper, Derek J. ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+
[9]  
Campeau LC, 2007, ALDRICHIM ACTA, V40, P35
[10]   Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].
Chatani, N ;
Asaumi, T ;
Yorimitsu, S ;
Ikeda, T ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10935-10941