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 H2 as the only byproduct, by employing an undivided cell with a graphite anode and a nickel cathode. The use of iodide as a...

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Bibliographic Details
Published in:ACS sustainable chemistry & engineering 2021-08, Vol.9 (34), p.11596-11603
Main Authors: Vanhoof, Jef R, De Smedt, Pieter J, Krasniqi, Besir, Ameloot, Rob, Sakellariou, Dimitrios, De Vos, Dirk E
Format: Article
Language:English
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Summary: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.
ISSN:2168-0485
2168-0485
DOI:10.1021/acssuschemeng.1c04473