Electrochemically Promoted Synthesis of N-Sulfonyl Sulfinimidate Esters and Sulfilimines from Sulfonamides, Thiophenols, Thioethers, and Alcohols

In this work, we report an electrochemical method for the straightforward preparation of scarcely accessible sulfinimidate esters from readily available sulfonamides, thiophenols, and alcohols. Mechanistic experiments show that sulfur oxidation at the anodic surface generates an electrophilic intermediate, which subsequently undergoes nucleophilic substitution. Moreover, sulfilimines can be obtained in moderate-to-excellent yields when thioethers are used as the S-donor instead of thiophenols via a dehydrogenateive imination process. This method is also characterized by mild reaction condition, operational simplicity, high atomic economic efficiency, easy later drug synthesis, and modification, as well as scaling up to a gram scale.