Environmentally Friendly Chemoselective Oxidation of Primary Aliphatic Amines by Using a Biomimetic Electrocatalytic System
Résumé
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 oxidases enzymes, these mediators exhibited lower reactivity with α-branched primary amines and no reactivity toward secondary amines. In the case of 3,4aminophenol derivatives which lack the 2hydroxyl group, the generated o-azaquinone species failed to catalyze the oxidation of the amine to the corresponding imine. Further mechanistic considerations allowed to justify the crucial role of the 2-hydroxyl group to convert a catalytic inert species into a highly effective biomimetic catalyst.
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martine-largeron Chem. Eur. J. 2008 accepted.pdf (177.03 Ko)
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