One-pot synthesis of heterocyclic compounds through insertion of alkynes into the PdC bond of activated cyclopalladated benzyl methyl sulphide

Abstract

Benzyl methyl sulphide is readily cyclopalladated by palladium acetate. Compared with the chloride bridged-derivative, the cationic cyclopalladated compounds are more reactive towards the insertion of alkyne into their PdC σ bonds, which leads in some cases to cationic organic heterocycles containing either a six- or an eight-membered ring, arising from insertion of one or two alkyne molecules, the CS bond being formed via reductive elimination of palladium(0).