Abstract
A method for generating alkynylmagnesium chlorides from 1-chlorovinyl p-tolyl sulfoxides and an isopropylmagnesium chloride–lithium chloride complex (turbo Grignard reagent) has been developed. The method consists of a sulfoxide/magnesium exchange reaction of 1-chlorovinyl p-tolyl sulfoxides and a turbo Grignard reagent, a Fritsch–Buttenberg–Wiechell rearrangement of the resulting magnesium alkylidene carbenoids, and a deprotonation of terminal alkynes with a turbo Grignard reagent. The resulting alkynylmagnesium chlorides are reacted with a variety of electrophiles to generate internal alkynes.
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