Electrochemical aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na

Abstract

Herein, we describe an electrochemical strategy that enables the aminotrideuteromethylthiolation of isocyanides with anilines and CD3SSO3Na, providing an unprecedented route to access S-CD3 isothioureas in satisfactory yields. Mechanistic studies reveal that the transformation initiates the addition of CD3S radical to the isocyanide followed by a nucleophilic attack of the in-situ generated imine carbocation intermediate with anilines. Importantly, these reactions exhibit exclusive chemo-selectivity at carbon of isocyanides, wide functional groups compatibility as well as late-stage functionalization of complex substrates.