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Issue 47, 2013
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Chemoenzymatic selective formation of C–N bonds in a benzimidazole heterocycle

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Abstract

A novel and efficient method for the chemoenzymatic selective formation of C–N bonds in the synthesis of a 2-substituted benzimidazole heterocycle, catalyzed by lipase from porcine pancreas (PPL), has been developed. A series of 2-substituted benzimidazole derivatives were synthesized under mild conditions, with high yields (89–96%) and high selectivity. The blank and control experiments reveal that PPL plays an important catalytic role during the selective C–N bond formation process. The results demonstrate that PPL has a broad catalytic tolerance towards different aldehydes containing electron-donating or -withdrawing groups in this reaction. This study provides an efficient tool for the selective formation of C–N bonds in the synthesis of 2-substituted benzimidazole derivatives.

Graphical abstract: Chemoenzymatic selective formation of C–N bonds in a benzimidazole heterocycle

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Publication details

The article was received on 29 Jul 2013, accepted on 19 Sep 2013 and first published on 25 Sep 2013


Article type: Paper
DOI: 10.1039/C3RA43982H
Citation: RSC Adv., 2013,3, 24959-24963
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    Chemoenzymatic selective formation of C–N bonds in a benzimidazole heterocycle

    H. Zheng, Q. Shi, K. Du, X. Cao and P. Zhang, RSC Adv., 2013, 3, 24959
    DOI: 10.1039/C3RA43982H

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