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.

Automated summary

Sulfur alkylation of N-acyl sulfenamides with alkyl halides leads to sulfilimines, with yields ranging from 47% to 98%. This reaction demonstrates a wide scope with different aryl and alkyl sulfenamides, as well as various N-acyl groups. Alkyl halides with different steric and electronic properties, including methyl, primary, secondary benzyl, and propargyl halides, are effective reactants. Furthermore, an asymmetric phase-transfer alkylation was successfully demonstrated. The resulting sulfilimine products can be easily converted to N-acyl and free sulfoximine, which are important motifs in medicinal chemistry.