Oxidative Olefination of Secondary Amines with Carbon Nucleophiles

被引：37

作者：

Zhang, Yong-Gang ^{[1
]}

Xu, Jing-Kun ^{[1
]}

Li, Xi-Ming ^{[1
]}

Tian, Shi-Kai ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 18期

基金：

中国国家自然科学基金;

关键词：

Homogeneous catalysis; Olefination; Oxidation; Amines; Imines; C-H BOND; N-BENZYLIC SULFONAMIDES; STEREOSELECTIVE-SYNTHESIS; 4-COMPONENT REACTION; GLYCINE DERIVATIVES; SULFONYL ALDIMINES; FACILE SYNTHESIS; ANIL SYNTHESIS; AZAARENES; CATALYST;

D O I：

10.1002/ejoc.201300368

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An unprecedented olefination reaction of secondary amines with carbon nucleophiles has been developed through C-N/C-H functionalization under metal-free oxidative conditions. In the presence of a stoichiometric amount of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), a range of secondary N-alkylanilines smoothly underwent oxidative olefination with 2-alkylazaarenes, acetophenone, and malononitrile to give structurally diverse polysubstituted alkenes in moderate to excellent yields with excellent (E) selectivity. Preliminary mechanistic studies revealed that the oxidative olefination reaction proceeds through amine oxidation followed by imine olefination.

引用

页码：3648 / 3652

页数：5

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