A regio- and stereoselective entry to (Z)-β-halo alkenyl sulfides and their applications to access stereodefined trisubstituted alkenes

Abstract

A mild and efficient preparation of (Z)-β-halo alkenyl sulfides via the K2CO3-promoted hydrothiolation of haloalkynes has been realized, producing (Z)-β-bromo and (Z)-β-chloro vinylic sulfides in high yields with excellent regio- and stereoselectivity. This approach covers a variety of substrates, including both aryl and alkyl haloalkynes. Meaningfully, it allows a facile access to stereodefined (Z)- or (E)-trisubstituted olefins featuring the iterative cross-coupling of carbon-halide and carbon-sulfur bonds of β-halo alkenyl sulfides.