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Article Dans Une Revue European Journal of Organic Chemistry Année : 2016

Catalytic Oxidative Coupling of Primary Amines under Air: A Flexible Route to Benzimidazole Derivatives

Résumé

Benzimidazoles are of fundamental importance in chemistry and biology, and the development of efficient environmentally benign methods for their preparation remains a key challenge for organic chemists. In a biomimetic approach inspired by copper amine oxidases, we disclose herein the scope and factors influencing the success of the cooperative action of CuBr2 electron transfer mediator and topaquinone-like substrate-selective catalyst in the oxidative cyclocondensation of primary amines with oaminoanilines. This one-pot atom-economical multistep process, that works under green conditions with ambient air as the terminal oxidant, low loadings of catalysts together with equimolar amounts of commercially available amine substrates, is particularly suitable for the preparation of 1,2-disubstituted benzimidazoles. Furthermore, it allows the functionalization of non-activated primary aliphatic amines that are known to be challenging substrates for non-enzymatic catalytic aerobic systems.
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Dates et versions

hal-02384649 , version 1 (21-11-2020)

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Khac Minh Huy Nguyen, Martine Largeron. Catalytic Oxidative Coupling of Primary Amines under Air: A Flexible Route to Benzimidazole Derivatives. European Journal of Organic Chemistry, 2016, 2016 (5), pp.1025-1032. ⟨10.1002/ejoc.201501520⟩. ⟨hal-02384649⟩
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