Coupling Reaction of Magnesium Alkylidene Carbenoids with α-Sulfonyl­allyllithiums: An Efficient Route to Multi-Substituted Vinylallenes

Abstract

A variety of vinylallenes were successfully synthesized from 1-chlorovinyl p-tolyl sulfoxides and allyl or vinyl sulfones. Allyl and vinyl sulfones served as α-sulfonylallyllithium sources were prepared from carbonyl compounds in three or four steps in good overall yields. The coupling reaction of α-sulfonylallyllithiums with magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides and isopropylmagnesium chloride, afforded multi-substituted vinylallenes in up to 88% yield.

Key words

vinylallenes - magnesium alkylidene carbenoids - allyl sulfones - vinyl sulfones - 1-chlorovinyl p-tolyl sulfoxides - coupling

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