Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst

A novel methodology is presented for preparing non-noble metal-based heterogeneous catalysts doped with low amounts of noble metals, yielding highly active and reusable materials for sustainable organic transformations. A new Co–Ru@C catalyst was developed by incorporating small ruthenium nanopartic...

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Autores: Río Rodríguez, José Luis del, Gutiérrez Tarriño, Silvia, Molina, María Asunción, Costley Wood, Lucy, Falcini, Chiara, Beale, Andrew M., Oña Burgos, Pascual
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2025
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/181836
Acceso en línea:https://hdl.handle.net/11441/181836
https://doi.org/10.1021/acssuschemeng.5c05806
Access Level:acceso abierto
Palabra clave:Heterogeneous catalysis
1,2-dinitroarenes
Cobalt carbon catalysts
Ruthenium doping
Hydrogenative coupling
Benzimidazoles
One-pot reactions
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spelling Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous CatalystRío Rodríguez, José Luis delGutiérrez Tarriño, SilviaMolina, María AsunciónCostley Wood, LucyFalcini, ChiaraBeale, Andrew M.Oña Burgos, PascualHeterogeneous catalysis1,2-dinitroarenesCobalt carbon catalystsRuthenium dopingHydrogenative couplingBenzimidazolesOne-pot reactionsA novel methodology is presented for preparing non-noble metal-based heterogeneous catalysts doped with low amounts of noble metals, yielding highly active and reusable materials for sustainable organic transformations. A new Co–Ru@C catalyst was developed by incorporating small ruthenium nanoparticles (1 wt %) and cobalt nanoparticles (10 wt %) on Vulcan carbon via pyrolysis of a ruthenium-doped cobalt metal–organic framework supported on carbon (2D-Co(Ru)MOF/C). Advanced characterization (in situ PXRD and XAS, HAADF-STEM, HRTEM) confirmed strong Co–Ru interactions, enhancing catalytic activity. The catalyst was evaluated in the one-pot reductive amination of dinitrobenzenes to benzimidazoles using molecular hydrogen and water, which is in line with green chemistry. The synergistic effect between Co and Ru enabled quantitative product yields under significantly milder reaction conditions than the existing ones. In addition, ruthenium was found to facilitate hydrogen activation in the bimetallic material compared with its undoped Co@C counterpart. Regarding stability, the Co–Ru@C catalyst retained its activity over at least five consecutive cycles without metal leaching or structural degradation. This material demonstrated a broad substrate scope, affording over 20 functionalized benzimidazoles in high yields. Half-gram-scale syntheses of commercial Diabazole and Fuberidazole further validated the scalability of this approach.American Chemical SocietyQuímica OrgánicaMinisterio de Ciencia e Innovación (MICIN). EspañaEuropean Union (UE)Generalitat Valenciana2025info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/181836https://doi.org/10.1021/acssuschemeng.5c05806reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésACS Sustainable Chemistry & Engineering, 13 (37), 15533-15546.CEX2021-001230-SPID2022140111OB-I00TED2021-130191B-C41PRTR-C17.I1MFA/ 2022/047https://doi.org/10.1021/acssuschemeng.5c05806info:eu-repo/semantics/openAccessoai:idus.us.es:11441/1818362026-06-17T12:51:07Z
dc.title.none.fl_str_mv Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
title Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
spellingShingle Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
Río Rodríguez, José Luis del
Heterogeneous catalysis
1,2-dinitroarenes
Cobalt carbon catalysts
Ruthenium doping
Hydrogenative coupling
Benzimidazoles
One-pot reactions
title_short Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
title_full Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
title_fullStr Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
title_full_unstemmed Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
title_sort Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalyst
dc.creator.none.fl_str_mv Río Rodríguez, José Luis del
Gutiérrez Tarriño, Silvia
Molina, María Asunción
Costley Wood, Lucy
Falcini, Chiara
Beale, Andrew M.
Oña Burgos, Pascual
author Río Rodríguez, José Luis del
author_facet Río Rodríguez, José Luis del
Gutiérrez Tarriño, Silvia
Molina, María Asunción
Costley Wood, Lucy
Falcini, Chiara
Beale, Andrew M.
Oña Burgos, Pascual
author_role author
author2 Gutiérrez Tarriño, Silvia
Molina, María Asunción
Costley Wood, Lucy
Falcini, Chiara
Beale, Andrew M.
Oña Burgos, Pascual
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Química Orgánica
Ministerio de Ciencia e Innovación (MICIN). España
European Union (UE)
Generalitat Valenciana
dc.subject.none.fl_str_mv Heterogeneous catalysis
1,2-dinitroarenes
Cobalt carbon catalysts
Ruthenium doping
Hydrogenative coupling
Benzimidazoles
One-pot reactions
topic Heterogeneous catalysis
1,2-dinitroarenes
Cobalt carbon catalysts
Ruthenium doping
Hydrogenative coupling
Benzimidazoles
One-pot reactions
description A novel methodology is presented for preparing non-noble metal-based heterogeneous catalysts doped with low amounts of noble metals, yielding highly active and reusable materials for sustainable organic transformations. A new Co–Ru@C catalyst was developed by incorporating small ruthenium nanoparticles (1 wt %) and cobalt nanoparticles (10 wt %) on Vulcan carbon via pyrolysis of a ruthenium-doped cobalt metal–organic framework supported on carbon (2D-Co(Ru)MOF/C). Advanced characterization (in situ PXRD and XAS, HAADF-STEM, HRTEM) confirmed strong Co–Ru interactions, enhancing catalytic activity. The catalyst was evaluated in the one-pot reductive amination of dinitrobenzenes to benzimidazoles using molecular hydrogen and water, which is in line with green chemistry. The synergistic effect between Co and Ru enabled quantitative product yields under significantly milder reaction conditions than the existing ones. In addition, ruthenium was found to facilitate hydrogen activation in the bimetallic material compared with its undoped Co@C counterpart. Regarding stability, the Co–Ru@C catalyst retained its activity over at least five consecutive cycles without metal leaching or structural degradation. This material demonstrated a broad substrate scope, affording over 20 functionalized benzimidazoles in high yields. Half-gram-scale syntheses of commercial Diabazole and Fuberidazole further validated the scalability of this approach.
publishDate 2025
dc.date.none.fl_str_mv 2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/181836
https://doi.org/10.1021/acssuschemeng.5c05806
url https://hdl.handle.net/11441/181836
https://doi.org/10.1021/acssuschemeng.5c05806
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv ACS Sustainable Chemistry & Engineering, 13 (37), 15533-15546.
CEX2021-001230-S
PID2022140111OB-I00
TED2021-130191B-C41
PRTR-C17.I1
MFA/ 2022/047
https://doi.org/10.1021/acssuschemeng.5c05806
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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