Palladium-catalyzed Fujiwara-Moritani Reaction with Vinylsilanes

The palladium-catalyzed Fujiwara-Moritani reaction with unactivated vinylsilane has been developed. The use of dimethyl sulfide as a ligand and air as the terminal oxidant was crucial for achieving the high catalytic activity. Dehydrogenative C-C bond formation was accomplished with indoles and pyrroles, and subsequent transformations exploiting the vinylsilane functionality of the products were demonstrated. Experimental studies indicated that the dimethyl sulfide ligand facilitates both catalyst reoxidation and olefin insertion steps.