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

被引:324
作者
Sromek, AW [1 ]
Rubina, M [1 ]
Gevorgyan, V [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
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
收藏
页码:10500 / 10501
页数:2
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