Palladium-Catalyzed Carbonylative Lactonization of Propargyl Alcohols with Organic Dichalcogenides and Carbon Monoxide

The reaction of propargylic alcohols with diaryl disulfides and carbon monoxide in the presence of tetrakis(triphenylphosphine)palladium leads to a novel thiolative lactonization to afford beta-(arylthio)-alpha,beta-unsaturated lactones in moderate to good yields. Similar conditions can be employed with homopropargylic alcohols, giving the corresponding delta-lactones with a beta-arylthio group successfully. The reaction using diaryl diselenides in lieu of diaryl disulfides also attains a similar one-pot thiolation/lactonization sequence to provide the corresponding beta-selenobutenolides (7).