Electrochemical Aziridination of Tetrasubstituted Alkenes with Ammonia

Abstract

Ammonia (NH3) is an ideal nitrogen source in terms of availability, reactivity, safety, atom economy, environmental compatibility, and ease of isolation. However, its utility for amine synthesis is limited by its high bond dissociation energy, its strong coordination ability, and the difference between its reactivity and that of the product amines. Herein, we reported the first electrochemical protocol for direct syntheses of unprotected tetrasubstituted aziridines with NH3 and alkenes in the absence of an oxidant, which are highly challenging to achieve by other methods. The combination of graphite felt as the anode material and MeOH as the solvent was the key to the success of the protocol, and the effects of these factors were investigated by means of cyclic voltammetry and density functional theory calculations.