Perfluoroalkylated Bis(sulfilimine)s and Bis(sulfoximine)s by a Ritter-Type Reaction

Our synthetic methodology, which was previously developed for the preparation of perfluoroalkyl sulfilimines by a reaction between fluorinated sulfoxides and nitriles, has been successfully extended to dinitriles. According to the reaction conditions, we can preferentially produce a cyano monosulfilimine or a bis(sulfilimine). New cyano thioethers have been synthesized through a rearrangement process. Mono- and bis(sulfilimine)s were also oxidized to afford the corresponding sulfoximines, which provide a direct route to potential new ligands for catalysis and new electrophilic perfluoroalkylating reagents.