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Direct Electrocatalytic N–H Aziridination of Aromatic Alkenes Using Ammonia

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journal contribution
posted on 18.08.2021, 16:44 by Jef R. Vanhoof, Pieter J. De Smedt, Besir Krasniqi, Rob Ameloot, Dimitrios Sakellariou, Dirk E. De Vos
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 H2 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 (I2) and NH3 creating NH2I as a reactive species involved in the aziridination.