Convenient One-Pot Synthesis of Vinylic Sulfides from Thioalkynes via a Catalytic Hydroboration-Coupling Sequence

A variety of vinylic sulfides are stereospecifically synthesized by the catalytic hydroboration of thioacetylenes with catecholborane followed by cross-coupling of the resulting boron derivatives with organic halides. The use of the same palladium catalyst for both stages allows the whole transformation to be carried out in one flask. The synthetic utility of the method is demonstrated by the transformation of vinylic sulfides into diene, indole, and naphtho[b]furan derivatives.