Radical Alkenylation of α-Halo Carbonyl Compounds with Alkenylindiums

Kazuaki Takami, Hideki Yorimitsu, and Koichiro Oshima*
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan
Org. Lett., 2004, 6 (24), pp 4555–4558
DOI: 10.1021/ol048070o
Publication Date (Web): October 27, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, oshima@orgrxn.mbox.media.kyoto-u.ac.jp

Abstract

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Alkenylation reaction of α-halo carbonyl compounds with alkenylindiums proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties as well as a styryl group could be introduced by this method. The geometry of the carbon−carbon double bonds of the alkenylindiums was retained. Preparation of an alkenylindium via a hydroindation of 1-alkyne followed by radical alkenylation established an efficient one-pot strategy.

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History

  • Published In Issue November 25, 2004
  • Received September 22, 2004

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