Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 5, Pages 1025-1032Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501520
Keywords
Homogeneous catalysis; Cross-coupling; Oxidation; Nitrogen heterocycles; Amines
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Funding
- Association pour le Developpement de la Recherche Appliquee a la Pharmacologie (ADRAPHARM)
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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 as electron-transfer mediator and a topaquinone-like substrate-selective catalyst in the oxidative cyclocondensation of primary amines with o-aminoanilines. This one-pot atom-economic multistep process, which works under green conditions with ambient air as the terminal oxidant, low loadings of catalyst, and equimolar amounts of commercially available amine substrates, is particularly suitable for the preparation of 1,2-disubstituted benzimidazoles. Furthermore, it allows the functionalization of nonactivated primary aliphatic amines, which are known to be challenging substrates for non-enzymatic catalytic aerobic systems.
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