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Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles

We investigated the catalytic efficacy of supported gold nanoparticles (AuNPs) towards the selective reaction between o-phenylenediamine and aldehydes that yields 2-substituted benzimidazoles. Among several supported gold nanoparticle platforms, the Au/TiO(2) provides a series of 2-aryl and 2-alkyl...

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Autores principales: Tzani, Marina A., Gabriel, Catherine, Lykakis, Ioannis N.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7760220/
https://www.ncbi.nlm.nih.gov/pubmed/33271922
http://dx.doi.org/10.3390/nano10122405
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author Tzani, Marina A.
Gabriel, Catherine
Lykakis, Ioannis N.
author_facet Tzani, Marina A.
Gabriel, Catherine
Lykakis, Ioannis N.
author_sort Tzani, Marina A.
collection PubMed
description We investigated the catalytic efficacy of supported gold nanoparticles (AuNPs) towards the selective reaction between o-phenylenediamine and aldehydes that yields 2-substituted benzimidazoles. Among several supported gold nanoparticle platforms, the Au/TiO(2) provides a series of 2-aryl and 2-alkyl substituted benzimidazoles at ambient conditions, in the absence of additives and in high yields, using the mixture CHCl(3):MeOH in ratio 3:1 as the reaction solvent. Among the AuNPs catalysts used herein, the Au/TiO(2) containing small-size nanoparticles is found to be the most active towards the present catalytic methodology. The Au/TiO(2) can be recovered and reused at least five times without a significant loss of its catalytic efficacy. The present catalytic synthetic protocol applies to a broad substrate scope and represents an efficient method for the formation of a C–N bond under mild reaction conditions. Notably, this catalytic methodology provides the regio-isomer of the anthelmintic drug, Thiabendazole, in a lab-scale showing its applicability in the efficient synthesis of such N-heterocyclic molecules at industrial levels.
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spelling pubmed-77602202020-12-26 Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles Tzani, Marina A. Gabriel, Catherine Lykakis, Ioannis N. Nanomaterials (Basel) Article We investigated the catalytic efficacy of supported gold nanoparticles (AuNPs) towards the selective reaction between o-phenylenediamine and aldehydes that yields 2-substituted benzimidazoles. Among several supported gold nanoparticle platforms, the Au/TiO(2) provides a series of 2-aryl and 2-alkyl substituted benzimidazoles at ambient conditions, in the absence of additives and in high yields, using the mixture CHCl(3):MeOH in ratio 3:1 as the reaction solvent. Among the AuNPs catalysts used herein, the Au/TiO(2) containing small-size nanoparticles is found to be the most active towards the present catalytic methodology. The Au/TiO(2) can be recovered and reused at least five times without a significant loss of its catalytic efficacy. The present catalytic synthetic protocol applies to a broad substrate scope and represents an efficient method for the formation of a C–N bond under mild reaction conditions. Notably, this catalytic methodology provides the regio-isomer of the anthelmintic drug, Thiabendazole, in a lab-scale showing its applicability in the efficient synthesis of such N-heterocyclic molecules at industrial levels. MDPI 2020-12-01 /pmc/articles/PMC7760220/ /pubmed/33271922 http://dx.doi.org/10.3390/nano10122405 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tzani, Marina A.
Gabriel, Catherine
Lykakis, Ioannis N.
Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles
title Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles
title_full Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles
title_fullStr Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles
title_full_unstemmed Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles
title_short Selective Synthesis of Benzimidazoles from o-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles
title_sort selective synthesis of benzimidazoles from o-phenylenediamine and aldehydes promoted by supported gold nanoparticles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7760220/
https://www.ncbi.nlm.nih.gov/pubmed/33271922
http://dx.doi.org/10.3390/nano10122405
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