S‐Trideuteromethylation of Sulfenamides: Synthesis of Trideuteromethyl Sulfilimines

In this study, we present a base‐mediated, metal‐free method for synthesizing trideuteromethyl sulfilimines, which are significant in organic and medicinal chemistry. Our approach involves the modification of sulfenamides and the use of an electrophilic trideuteromethylating reagent under anionic conditions. This method has been successfully applied to a wide range of sulfenamides, generally providing the desired products in good yields and effective deuteration rates. Through detailed mechanistic studies, we have determined that the reaction proceeds without a free radical pathway. Our findings contribute to advancing the methodology for sulfilimine synthesis, underlining its relevance in modern chemical research.