1,2-Halogen migration in haloallenyl ketones: Regiodivergent synthesis of halofurans

被引：326

作者：

Sromek, AW ^{[1
]}

Rubina, M ^{[1
]}

Gevorgyan, V ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 30期

关键词：

D O I：

10.1021/ja053290y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Selective 1,2-iodine, bromine, and chlorine migration in haloallenyl ketones in the presence of Au catalyst has been demonstrated. It was found that, depending on the nature of the Au catalyst used, either selective bromine migration or hydrogen shift occurs, leading to the formation of 3- or 2-bromofurans, respectively. Halirenium intermediate was proposed for the unusual 1,2-halogen migration. This cascade transformation allows for mild and efficient synthesis of various types of 3-halofurans. Copyright © 2005 American Chemical Society.

引用

页码：10500 / 10501

页数：2

共 38 条

[31] 5-Endo-dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones:: Regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans [J].