Copper-Catalyzed Dehydrogenative Cross-Coupling Reaction between Allylic C-H Bonds and α-C-H Bonds of Ketones or Aldehydes

被引：24

作者：

Huang, Xing-Fen ^{[1
]}

Salman, Muhammad ^{[1
]}

Huang, Zhi-Zhen ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 22期

基金：

中国国家自然科学基金;

关键词：

aldehyde; allylic; CH bonds; coupling reactions; ketones; CONJUGATE ADDITION; ALKYLATION; PALLADIUM; ACTIVATION; COMPLEXES; OLEFINS;

D O I：

10.1002/chem.201402114

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A dehydrogenative cross-coupling reaction between allylic CH bonds and the -CH bond of ketones or aldehydes was developed using Cu(OTf)(2) as a catalyst and DDQ as an oxidant. This synthetic approach to ,-unsaturated ketones and aldehydes has the advantages of broad scope for both ketones and aldehydes as reactants, mild reaction conditions, good yields and atom economy. A plausible mechanism using Cu(OTf)(2) as a Lewis acid catalyst was also proposed (DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone; Tf=trifluoromethanesulfonate).

引用

页码：6618 / 6621

页数：4

共 37 条

[1] Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].

Alexakis, A. ;

Backvall, J. E. ;

Krause, N. ;

Pamies, O. ;

Dieguez, M. .

CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823

[2] Molybdenum-catalyzed asymmetric allylic alkylations [J].

Belda, O ;

Moberg, C .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (03) :159-167

[3] Highly efficient metal-free cross-coupling by C-H activation between allylic and active methylenic compounds promoted by DDQ [J].

Cheng, Dongping ;

Bao, Weiliang .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) :1263-1266

[4] Copper-catalyzed asymmetric allylic alkylation [J].

Falciola, Caroline A. ;

Alexakis, Alexandre .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (22) :3765-3780

[5] Catalytic asymmetric conjugate addition and allylic alkylation with Grignard reagents [J].

Harutyunyan, Syuzanna R. ;

den Hartog, Tim ;

Geurts, Koen ;

Minnaard, Adriaan J. ;

Feringa, Ben L. .

CHEMICAL REVIEWS, 2008, 108 (08) :2824-2852

[6]

Kelleher R. G., 1980, J CHEM SOC CHEM COMM, V134, P486

[7] Development of novel Lewis acid catalysts for selective organic reactions in aqueous media [J].

Kobayashi, S ;

Manabe, K .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (04) :209-217

[8] Green chemistry: The development of cross-dehydrogenative coupling (CDC) for chemical synthesis [J].

Li, Chao-Jun ;

Li, Zhiping .

PURE AND APPLIED CHEMISTRY, 2006, 78 (05) :935-945

[9] Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].

Li, Chao-Jun .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :335-344

[10] Catalytic allylic alkylation via the cross-dehydrogenative-coupling reaction between allylic sp3 C-H and methylenic sp3 C-H bonds [J].

Li, ZP ;

Li, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :56-57

← 1 2 3 4 →