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

Ying-Ying Qin; Yan-Yan Yang; Xiao-Long Qiu; Feng-Ling Qing

doi:10.1055/s-2006-926420

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

Ying-Ying Qin^a, Yan-Yan Yang^b, Xiao-Long Qiu^b, 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;

Abstract

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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.

Key words

radical deselenylation - radical addition - organoselenium compounds - bromodifluoromethyl phenyl selenide

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