Preparation of Sulfilimines by Sulfur-Alkylation of N-Acyl Sulfenamides with Alkyl Halides

Sulfur alkylation of N-acyl sulfenamideswithalkyl halides provides sulfilimines in 47% to 98% yields. A broadscope was established with a variety of aryl and alkyl sulfenamides,including for different N-acyl groups. Alkyl halideswith different steric and electronic properties were effective inputs,including methyl, primary, secondary, benzyl, and propargyl halides.A proof-of-concept asymmetric phase-transfer alkylation was also demonstrated. A sulfilimine productwas readily converted to an N-acyl and to a freesulfoximine, which represent important motifs in medicinal chemistry.