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

Sulfur alkylation of N -acyl sulfenamides with alkyl halides provides sulfilimines in 47% to 98% yields. A broad scope was established with a variety of aryl and alkyl sulfenamides, including for different N -acyl groups. Alkyl halides with 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 product was readily converted to an N -acyl and to a free sulfoximine, which represent important motifs in medicinal chemistry.