Direct electrosynthesis of aromatic nitriles from methylarenes with hydroxylamine as a nitrogen source

Abstract

In this work, we present a novel electrochemical strategy for the direct conversion of methylarenes to aromatic nitriles, employing hydroxylamine sulfate as a safe, green, and economical nitrogen source. This transformation proceeds in an undivided cell without the need for transition-metal catalysts, chemical oxidants, or dehydrating agents, enabling efficient conversion of inert methylarenes into valuable aromatic nitrile compounds. Notably, this approach effectively circumvents the use of highly toxic cyanating reagents typically required in conventional nitrile synthesis. The practicality and potential application value of this methodology are demonstrated through gram-scale reactions and diverse derivatization of the cyano group. This electrochemical protocol not only provides a new strategy for constructing aryl nitriles but also expands the synthetic scope of electrochemical C–H functionalization.