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

[EN] 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 nanop...

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Autores: del Río-Rodríguez, Jose Luis, Molina, Maria Asunción, Costley-Wood, Lucy, Falcini, Chiara, Beale, Andrew M., Gutiérrez-Tarriño, Silvia, Oña-Burgos, Pascual|||0000-0002-2341-7867
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universitat Politècnica de València (UPV)
Repositorio:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
Idioma:inglés
OAI Identifier:oai:riunet.upv.es:10251/228461
Acceso en línea:https://riunet.upv.es/handle/10251/228461
Access Level:acceso abierto
Palabra clave:1,2-dinitroarenes
Benzimidazoles
Cobalt carbon catalysts
Heterogeneous catalysis
Hydrogenative coupling
One-pot reactions
Ruthenium doping
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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
del Río-Rodríguez, Jose Luis
1,2-dinitroarenes
Benzimidazoles
Cobalt carbon catalysts
Heterogeneous catalysis
Hydrogenative coupling
One-pot reactions
Ruthenium doping
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 del Río-Rodríguez, Jose Luis
Molina, Maria Asunción
Costley-Wood, Lucy
Falcini, Chiara
Beale, Andrew M.
Gutiérrez-Tarriño, Silvia
Oña-Burgos, Pascual|||0000-0002-2341-7867
author del Río-Rodríguez, Jose Luis
author_facet del Río-Rodríguez, Jose Luis
Molina, Maria Asunción
Costley-Wood, Lucy
Falcini, Chiara
Beale, Andrew M.
Gutiérrez-Tarriño, Silvia
Oña-Burgos, Pascual|||0000-0002-2341-7867
author_role author
author2 Molina, Maria Asunción
Costley-Wood, Lucy
Falcini, Chiara
Beale, Andrew M.
Gutiérrez-Tarriño, Silvia
Oña-Burgos, Pascual|||0000-0002-2341-7867
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Instituto Universitario Mixto de Tecnología Química
Departamento de Química
Escuela Técnica Superior de Ingeniería Industrial
European Commission
Generalitat Valenciana
Ministerio de Universidades
Agencia Estatal de Investigación
European Regional Development Fund
Ministerio de Ciencia e Innovación
Universitat Politècnica de València
Repositorio Institucional de la Universitat Politècnica de València Riunet
dc.subject.none.fl_str_mv 1,2-dinitroarenes
Benzimidazoles
Cobalt carbon catalysts
Heterogeneous catalysis
Hydrogenative coupling
One-pot reactions
Ruthenium doping
topic 1,2-dinitroarenes
Benzimidazoles
Cobalt carbon catalysts
Heterogeneous catalysis
Hydrogenative coupling
One-pot reactions
Ruthenium doping
description [EN] 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
2025-09-22
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://riunet.upv.es/handle/10251/228461
url https://riunet.upv.es/handle/10251/228461
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2022-140111OB-I00 HACIA EL GREEN DEAL: SINERGIAS ENTRE CATALISIS HETEROGENEA Y HOMOGENEA PARA LA PRODUCCION SELECTIVA DE COMPUESTOS QUIMICOS ORGANOALQUILO DESDE FUENTES C1 RENOVA
European Commission https://doi.org/10.13039/501100000780 H2020 101022507 Selective CO2 conversion to renewable methanol through innovative heterogeneous catalyst systems optimized for advanced hydrogenation technologies (microwave, plasma and magnetic induction).
Universitat Politècnica de València https://doi.org/10.13039/501100004233 PAID-06-24 Ayuda a Primeros Proyectos de Investigación (PAID-06-24)
Universitat Politècnica de València https://doi.org/10.13039/501100004233 PAID-10-23
Generalitat Valenciana https://doi.org/10.13039/501100003359 MFA%2F2022%2F047
Ministerio de Universidades MIU FPU21%2F02562
Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 CEX2021-001230-S
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 TED2021-130191B-C41 Conversión de energía en productos químicos mediante la producción de H2 acoplada con la captura y conversión de CO2: subproyecto 1
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reconocimiento (by)
http://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reconocimiento (by)
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
instname:Universitat Politècnica de València (UPV)
instname_str Universitat Politècnica de València (UPV)
reponame_str RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
collection RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
repository.name.fl_str_mv
repository.mail.fl_str_mv
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spelling Green One-Pot Synthesis of Benzimidazoles from Dinitroarenes in Water Using a Ru-Doped Co-Based Heterogeneous Catalystdel Río-Rodríguez, Jose LuisMolina, Maria AsunciónCostley-Wood, LucyFalcini, ChiaraBeale, Andrew M.Gutiérrez-Tarriño, SilviaOña-Burgos, Pascual|||0000-0002-2341-78671,2-dinitroarenesBenzimidazolesCobalt carbon catalystsHeterogeneous catalysisHydrogenative couplingOne-pot reactionsRuthenium doping[EN] 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.Financial support from the Spanish Ministry of Science and Innovation (CEX2021-001230-S grant funded by MCIN/AEI/10.13039/501100011033) is gratefully acknowledged. The authors thank the financial support provided by the grants (PID2022140111OB-I00, TED2021-130191B-C41 funded by MCIN/AEI/10.13039/501100011033 and ERDF A way for making Europe and European Union NextGenerationEU/PRTR). This project has also received funding from the European Union's Horizon 2020 research and innovation program under grant agreement No. 101022507 and NextGenerationEU/PRTR. This study forms part of the Advanced Materials program and was supported by MCIN with partial funding from European Union Next Generation EU (PRTR-C17.I1) and by Generalitat Valenciana (MFA/2022/047). This work was also funded by "Ayuda a Primeros Proyectos de Investigacion (PAID-06-24)", Vicerectorate of Research of the Universitat Politecnica de Valencia (UPV). S.G.T. thanks the Universitat Politecnica de Valencia for her postdoctoral contract PAID-10-23. J.L.R.-R. thanks the MCIU for his FPU PhD contract FPU21/02562. XAS and XRD experiments were performed at NOTOS beamline at ALBA Synchrotron (proposal number 2023097780) with the collaboration of ALBA staff (Eduardo Villalobos and Carlo Marini). The authors thank Diamond Light Source, particularly B18 beamline team and D. Gianolio for their support during XAS measurement (proposal SP42561-1). The electron microscopy service of the UPV is acknowledged for their help in sample characterization.American Chemical SocietyInstituto Universitario Mixto de Tecnología QuímicaDepartamento de QuímicaEscuela Técnica Superior de Ingeniería IndustrialEuropean CommissionGeneralitat ValencianaMinisterio de UniversidadesAgencia Estatal de InvestigaciónEuropean Regional Development FundMinisterio de Ciencia e InnovaciónUniversitat Politècnica de ValènciaRepositorio Institucional de la Universitat Politècnica de València Riunet20252025-09-22journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://riunet.upv.es/handle/10251/228461reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valénciainstname:Universitat Politècnica de València (UPV)InglésengAgencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023 PID2022-140111OB-I00 HACIA EL GREEN DEAL: SINERGIAS ENTRE CATALISIS HETEROGENEA Y HOMOGENEA PARA LA PRODUCCION SELECTIVA DE COMPUESTOS QUIMICOS ORGANOALQUILO DESDE FUENTES C1 RENOVAEuropean Commission https://doi.org/10.13039/501100000780 H2020 101022507 Selective CO2 conversion to renewable methanol through innovative heterogeneous catalyst systems optimized for advanced hydrogenation technologies (microwave, plasma and magnetic induction).Universitat Politècnica de València https://doi.org/10.13039/501100004233 PAID-06-24 Ayuda a Primeros Proyectos de Investigación (PAID-06-24)Universitat Politècnica de València https://doi.org/10.13039/501100004233 PAID-10-23Generalitat Valenciana https://doi.org/10.13039/501100003359 MFA%2F2022%2F047Ministerio de Universidades MIU FPU21%2F02562Agencia Estatal de Investigación http://dx.doi.org/10.13039/501100011033 CEX2021-001230-SMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 TED2021-130191B-C41 Conversión de energía en productos químicos mediante la producción de H2 acoplada con la captura y conversión de CO2: subproyecto 1open accesshttp://purl.org/coar/access_right/c_abf2Reconocimiento (by)http://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:riunet.upv.es:10251/2284612026-06-13T07:49:27Z
score 15.812429

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