Synthesis 2006(9): 1475-1479  
DOI: 10.1055/s-2006-926420
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reductive Radical Reaction of gem-Difluorinated Organoselenium Compounds with an Indium(III) Chloride-Sodium Borohydride System

Ying-Ying Qina, Yan-Yan Yangb, Xiao-Long Qiub, Feng-Ling Qing*a,b
a College of Chemistry and Chemical Engineering, Donghua University, 1882 West Yanan Lu, Shanghai 200051, P. R. of China
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: flq@mail.sioc.ac.cn;
Further Information

Publication History

Received 9 November 2005
Publication Date:
04 April 2006 (eFirst)

Abstract

As for gem-difluorinated phenylseleno compounds, indium hydride, in situ generated by transmetallation between InCl3 and NaBH4, was found to be a convenient radical reagent as an alternative to tributyltin hydride. Besides its excellent performance in intramolecular cyclization and radical deselenylation, the NaBH4/InCl3 system also succeeded in intermolecular radical addition between organoselenium compounds and styrene.

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