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Article Dans Une Revue Chemistry - A European Journal Année : 2008

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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hal-02384952 , version 1 (27-11-2020)

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Martine Largeron, Angèle Chiaroni, Maurice-Bernard Fleury. Environmentally Friendly Chemoselective Oxidation of Primary Aliphatic Amines by Using a Biomimetic Electrocatalytic System. Chemistry - A European Journal, 2008, 14 (3), pp.996-1003. ⟨10.1002/chem.200700876⟩. ⟨hal-02384952⟩
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