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Updated: Jul 10, 2026

Electrochemically and Bioelectrochemically Induced Ammonium Recovery
Published on: January 22, 2015
Environmentally friendly chemoselective oxidation of primary aliphatic amines by using a biomimetic electrocatalytic
Martine Largeron1, Angèle Chiaroni, Maurice-Bernard Fleury
1UMR 8638 CNRS-Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4, avenue de L'Observatoire, 75270 Paris Cedex 06, France. martine.largeron@uni-paris5.fr
Abstract:
Environmentally friendly oxidation of primary aliphatic amines to imines has been successfully achieved, under metal-free conditions, by the use of diverse electrogenerated o-azaquinone mediators. High catalytic performance, together with high chemoselectivity, were observed with electron-poor o-azaquinone catalysts generated from 2-aminoresorcinol derivatives. Similar to copper amine oxidase enzymes, these mediators exhibited lower reactivity toward alpha-branched primary amines and no reactivity toward secondary amines. In the case of 3,4-aminophenol derivatives lacking a 2-hydroxy group, the generated o-azaquinone species failed to catalyze the oxidation of the amine to the corresponding imine. Further mechanistic considerations allowed a rationalization of the crucial role of the 2-hydroxy group in converting a catalytically inert species into a highly effective biomimetic catalyst.
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