Direct Electrocatalytic N-H Aziridination Of Aromatic Alkenes Using Ammonia

The electrocatalytic N-H aziridination of simple aromatic alkenes is reported, using ammonia (NH3) as an atom-efficient nitrogen source. Yields of up to 98% are achieved, with H-2 as the only byproduct, by employing an undivided cell with a graphite anode and a nickel cathode. The use of iodide as a redox mediator is essential to obtain the desired products. Mechanistic studies (cyclic voltammetry and multiple NMR techniques) reveal interactions between anodically formed iodine (I-2) and NH3 creating NH2I as a reactive species involved in the aziridination.