Reductive addition of propargylic acetates to carbonyl compounds proceeded smoothly at room temperature by using SmI2 and a catalytic amount of Pd(PPh3)4 to give the corresponding acetylenic and/or allenic alcohols with appreciable selectivity. The method is useful especially for the preparation of tri- and tetrasubstituted allenic alcohols.
A highly regioselective reaction of propargylic phosphates has been established by using SmI2 and a Pd(0) catalyst to give allenes and acetylenes in high isolated yields depending on the substrate used.