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Regio- and stereoselective addition of a silyl-substituted alkynyl sulfide to various terminal alkynes proceeds in the presence of a palladium catalyst to give (Z)-1-thio-1,3-enynes, which are useful building blocks for the synthesis of polysubstituted 1,3-enynes. Addition to internal alkynes also takes place under solvent-free conditions (see scheme).
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Iwasaki et al. (2011) studied this question.
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