Copper Powder-Catalyzed Regio- and Stereoselective Aminobromination of α,β-Unsaturated Ketones with TsNH2 and NBS as Nitrogen and Halogen Sources

被引：65

作者：

Chen, Zhan-Guo ^{[1
]}

Wei, Jun-Fa ^{[1
]}

Li, Run-Tao ^{[2
]}

Shi, Xian-Ying ^{[1
]}

Zhao, Peng-Fei ^{[1
]}

机构：

[1] Shaanxi Normal Univ, Sch Chem & Mat Sci, Xian 710062, Peoples R China

[2] Peking Univ, Sch Pharmaceut Sci, Beijing 100083, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 03期

关键词：

ELECTROPHILIC DIAMINATION; ALKENES; AMINOHALOGENATION; OLEFINS; COMPLEX;

D O I：

10.1021/jo8023768

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regio- and stereoselective aminobromination of alpha,beta-unsaturated ketones catalyzed by copper powder has been established with 4-TsNH2 and NBS as the nitrogen/bromine sources, respectively. This method provides an easy access for preparation of vicinal aminohalo derivatives in the presence of I mol % catalyst. Electron-rich alpha,beta-unsaturated ketones afforded the corresponding aminobrominated products in excellent yields (up to 99.8%), revealing that the addition has an electrophilic feature.

引用

页码：1371 / 1373

页数：3

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