A Metalloenzyme-Like Catalytic System for the Chemoselective Oxidative Cross-Coupling of Primary Amines to Imines under Ambient Conditions - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2015

A Metalloenzyme-Like Catalytic System for the Chemoselective Oxidative Cross-Coupling of Primary Amines to Imines under Ambient Conditions

Résumé

The direct oxidative cross-coupling of primary amines is a challenging transformation as homocoupling is usually preferred. We report herein the chemoselective preparation of cross-coupled imines through the synergistic combination of low loadings of Cu II metal-catalyst and o-iminoquinone organocatalyst under ambient conditions. This homogeneous cooperative catalytic system has been inspired by the reaction of copper amine oxidases, a family of metalloenzymes with quinone organic cofactors that mediate the selective oxidation of primary amines to aldehydes. After optimization, the desired cross-coupled imines are obtained in high yields with broad substrate scope through a transamination process, that leads to the homocoupled imine intermediate, followed by dynamic transimination. The ability to carry out the reactions, at room temperature, with ambient air rather than molecular oxygen as the oxidant and equimolar amounts of each coupling partner, is particularly attractive from an environmentally viewpoint.
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Dates et versions

hal-02384694 , version 1 (21-11-2020)

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Martine Largeron, Maurice-Bernard Fleury. A Metalloenzyme-Like Catalytic System for the Chemoselective Oxidative Cross-Coupling of Primary Amines to Imines under Ambient Conditions. Chemistry - A European Journal, 2015, 21 (9), pp.3815-3820. ⟨10.1002/chem.201405843⟩. ⟨hal-02384694⟩
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