Synthesis of sulfilimines via electron donor–acceptor complexes

Abstract

Sulfur-containing compounds have broad application prospects in chemical biology and medicinal chemistry. Herein we have reported Cu-catalyzed sulfilimine synthesis via arylation, alkylation and alkenylation of sulfenamides using readily accessible thianthrenium salts. The protocol allows a universal modular late-stage sulfilimination of highly functionalized molecules, and the sulfilimine motif can be easily transformed into sulfoximine and sulfondiimine derivatives. Mechanistic studies suggest that the bifunctional Cu catalyst plays an important role in the reaction, facilitating both the EDA association and the C–S coupling.