Vinyl sulfides, or enol thioethers, are surrogates of enol ethers and versatile synthetic intermediates applicable to a wide range of useful transformations. They are typically made by hydrothiolation of alkynes, cross-coupling of thiols with vinyl halides, or addition of thiols to carbonyls. Lesser known is their preparation via Wittig chemistry using ylides made from α-thioalkyl phosphonium salts. This presentation will describe our development of a new synthetic methodology that yields these thioalkyl phosphonium salts, via an efficient Pummerer rearrangement approach. We have also optimized subsequent Wittig transformations to prepare a diverse range of vinyl sulfides. Also presented will be an overview of new vinyl sulfide-based synthetic methods now under development in our laboratory.

Vinyl sulfides: New preparations and reactions

2019 Fall National Meeting

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