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The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

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Abstract

The tandem synthesis of benzimidazole and other azoles can be achived by the N-formylation of ortho-substituted anilines followed by a cyclization reaction. However, CO2-based N-formylations with hydrosilane reducing agents are base catalyzed whereas the cyclization reaction is acid catalyzed. The mismatch in catalytic conditions means that only one of the steps can be catalyzed in a single pot reaction. While the N-formylation reaction is frequently the target of catalyst development, the cyclization reaction requires comparably much harsher reaction conditions. Identification of these difficulties lead us to the development of a one-pot, two-step synthesis of benzimidazole under mild reaction conditions employing acid catalysts.

Graphical abstract: The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

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Publication details

The article was received on 08 Aug 2019, accepted on 08 Oct 2019 and first published on 08 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC06156H
Chem. Commun., 2019, Advance Article

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    The dilemma between acid and base catalysis in the synthesis of benzimidazole from o-phenylenediamine and carbon dioxide

    M. Hulla, S. Nussbaum, A. R. Bonnin and P. J. Dyson, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC06156H

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