One-Pot Synthesis of Aryl- and Alkyl S-Perfluoroalkylated NH-Sulfoximines from Sulfides

A general efficient one-pot synthesis of S-perfluoroalkylated NH-sulfoximines from sulfides has been developed using phenyliodine diacetate (PIDA) and ammonium carbamate. Remarkable rate enhancement with trifluoroethanol was observed, presumably due to H-bonding effects. These mild and metal-free conditions are compatible with -CH2F, -CFCl2, -CF2H, -CF2Br, -C4F9, and -CF3 groups, in both the alkyl- and aryl series. Based on a F-19 NMR analysis, a lambda(6)-acetoxysulfanenitrile intermediate was proposed.