Superbase-Mediated gem -Difluoroalkenylations of Sulfoximines.

At ambient temperature, deprotonated sulfoximines react with 1-trifluoromethylalkenes to provide either N- or C- gem -difluoroalkenylated products. The reaction site depends upon the N substituent of the starting material. The optimal conditions involve the use of a superbasic system NaOH in dimethyl sulfoxide. The reactions are characterized by a broad substrate scope and medium to high yields. Scale-up experiments of both the N- and C- gem -difluoroalkenylations proceeded well. Treatment of a N -difluoroallyl sulfoximine with an aryl thiol under dioxygen afforded the corresponding oxygenated addition product.