Synthesis of N-Alkenyl and N-Alkynyl S-Perfluoroalkylated Sulfoximines by Copper Catalysis

The introduction of a double or triple bond to the nitrogen atom of S-perfluoroalkyl sulfoximines is described. We propose a simple catalytic system based on copper iodide for the reaction with bromoalkenes and bromoalkynes, and based on copper dichloride for the coupling with terminal alkynes. The fluorinated chain was varied from perfluorobutyl to monofluoromethyl. The reaction proceeds efficiently when the unsaturated system is substituted by an aryl or alkyl group. In particular, aliphatic terminal alkynes are efficient substrates for this transformation.