Investigation of the Selectivity of the Palladium-Catalyzed Aroylation and Arylation of Stannyl Glycals with Aroyl Chlorides.

The selectivity of the palladium-catalyzed aroylation and arylation of 1-tributylstannyl glycals with aroyl chlorides was investigated. The selectivity was controlled by the palladium catalyst, and high selectivity was achieved via ligand modification of the palladium catalyst. The reaction catalyzed by Pd(OAc)2 provided aroyl C-glycals with high selectivity, whereas the reaction catalyzed by Pd(PPh3)4 produced aryl C-glycals with diminished selectivity. The scope and limitation of the selectivity in this reaction are discussed.