Cyclic Sulfoximines as Methyl and Perdeuteromethyl Transfer Agents and Their Applications in Photoredox Catalysis

Abstract

Benzo[1,3,2]dithiazole‐1,1,3‐trioxides are bench‐stable and easy‐to‐use reagents. In photoredox catalysis, they generate methyl and perdeuteromethyl radicals which can add to a variety of radical acceptors, including olefins, acrylamides, quinoxalinones, isocyanides, enol silanes, and N‐Ts acrylamide. As byproduct, a salt is formed which can be regenerated to the original methylating agent. Flow chemistry provides an option for reaction scale‐up further underscoring the synthetic usefulness of these methylation reagents. Mechanistic investigations suggest a single‐electron transfer (SET) pathway induced by photoredox catalysis.