One-Pot Synthesis of Aryl- and Alkyl S-Perfluoroalkylated NH-Sulfoximines from Sulfides.
Slim ChaabouniJean-François LohierAnne-Laure BarthelemyThomas GlachetElsa AnselmiGuillaume DagoussetPatrick DiterBruce PégotEmmanuel MagnierVincent ReboulPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2018)
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 -CH2 F, -CFCl2 , -CF2 H, -CF2 Br, -C4 F9 , and -CF3 groups, in both the alkyl- and aryl series. Based on a 19 F NMR analysis, a λ6 -acetoxysulfanenitrile intermediate was proposed.