Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes

被引：184

作者：

Basle, Olivier ^{[1
]}

Bidange, Johan ^{[1
]}

Shuai, Qi ^{[1
]}

Li, Chao-Jun ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 07期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

acylation; aliphatic aldehydes; C-H functionalization; oxidative cross-coupling; palladium catalysis; GLYCINE DERIVATIVES; DIRECT ARYLATION; FUNCTIONALIZATION; ALKYLATION; DECARBONYLATION; ACTIVATIONS; CHLORIDES; KETONES; OXYGEN;

D O I：

10.1002/adsc.200900874

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient method was developed for the direct acylation of arene sp(2) C-H bonds with aldehydes using palladium acetate as catalyst and peroxide as oxidant. The solvent-free oxidative acylation reaction assisted by a pyridine directing group provides an easy access to aromatic, aliphatic, and optical active ketones.

引用

页码：1145 / 1149

页数：5

共 35 条

[1]

[Anonymous], 2008, ANGEW CHEM

[2] Chelating N-Heterocyclic Carbene Alkoxide as a Supporting Ligand for PdII/IV C-H Bond Functionalization Catalysis [J].

Arnold, Polly L. ;

Sanford, Melanie S. ;

Pearson, Stephen M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (39) :13912-+

[3] 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

[4] 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

[5] Ru-3(CO)(12)-catalyzed coupling of heteroaromatic C-H/CO/olefins. Regioselective acylation of the imidazole ring [J].

Chatani, N ;

Fukuyama, T ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) :493-494

[6]

Chen X., 2009, ANGEW CHEM, V121, P5196

[7] 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

[8] 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

[9] Ruthenium-catalyzed oxidative cross-coupling of chelating arenes and cycloalkanes [J].

Deng, Guojun ;

Zhao, Liang ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (33) :6278-6282

[10] Sc(OTf)3-Catalyzed Direct Alkylation of Quinolines and Pyridines with Alkanes [J].

Deng, Guojun ;

Li, Chao-Jun .

ORGANIC LETTERS, 2009, 11 (05) :1171-1174

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