Synthesis of Sulfilimines via Multicomponent Reaction of Arynes, Sulfamides, and Thiosulfonates

Org Lett. 2023 Aug 25;25(33):6133-6138. doi: 10.1021/acs.orglett.3c02217. Epub 2023 Aug 14.

Abstract

In this work, a facile and efficient method for the synthesis of sulfilimines through multicomponent reaction of arynes, sulfamides, and thiosulfonates was developed. A variety of structurally diverse substrates and functional groups were very compatible in the reaction, giving the corresponding sulfilimines in good to high yields. This protocol could be conducted on a gram scale, and the product was easily converted to sulfide and sulfoximine. Mechanism studies revealed that sulfenamide generated in situ is the key intermediate for the reaction.