Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support

Autores
Marti, L.; Sánchez, Laura Mabel; Climent, María J.; Corma, A.; Iborra, S.; Romanelli, Gustavo Pablo; Concepcion, P.
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
2,1-Benzisoxazoles have been selectively synthesized through reductive heterocyclization of 2-nitroacylarenes using Pt-supported nanoparticles. The reaction involves a cascade process in which the first step is the reduction of the nitro group into hydroxylamine followed by heterocyclization through the nucleophilic attack of the hydroxylamine group to the carbonyl of the acyl group and further dehydration. The reaction was performed on Pt/C, Pt/TiO₂, and Pt/MgO using hydrogen as the reducing agent under mild reaction conditions. The results showed that Pt/MgO was the most active and selective catalyst. The study of the influence of the crystal size of the metal on the activity and selectivity, combined with the reaction mechanism examined by in situ Fourier transform infrared spectroscopy of the adsorbed reactant, showed that the maximum activity and selectivity to the target compound can be achieved by controlling the architecture of metal particles and acid–base properties of the support. The effect of temperature on selectivity, the stability of the Pt/MgO catalyst, and the scope of the reaction have been studied. Finally, reductive heterocyclization using different metals (Pd and Au) supported on MgO has also been performed.
Centro de Investigación y Desarrollo en Ciencias Aplicadas
Materia
Ciencias Exactas
Química
Reductive heterocyclization
2,1-benzisoxazole
Pt/MgO
2-nitroacylarenes
Cascade process
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/104962
Acceder
id SEDICI_20500dbb66cb7c17fb5016a45df96669
oai_identifier_str oai:sedici.unlp.edu.ar:10915/104962
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the SupportMarti, L.Sánchez, Laura MabelCliment, María J.Corma, A.Iborra, S.Romanelli, Gustavo PabloConcepcion, P.Ciencias ExactasQuímicaReductive heterocyclization2,1-benzisoxazolePt/MgO2-nitroacylarenesCascade process2,1-Benzisoxazoles have been selectively synthesized through reductive heterocyclization of 2-nitroacylarenes using Pt-supported nanoparticles. The reaction involves a cascade process in which the first step is the reduction of the nitro group into hydroxylamine followed by heterocyclization through the nucleophilic attack of the hydroxylamine group to the carbonyl of the acyl group and further dehydration. The reaction was performed on Pt/C, Pt/TiO₂, and Pt/MgO using hydrogen as the reducing agent under mild reaction conditions. The results showed that Pt/MgO was the most active and selective catalyst. The study of the influence of the crystal size of the metal on the activity and selectivity, combined with the reaction mechanism examined by in situ Fourier transform infrared spectroscopy of the adsorbed reactant, showed that the maximum activity and selectivity to the target compound can be achieved by controlling the architecture of metal particles and acid–base properties of the support. The effect of temperature on selectivity, the stability of the Pt/MgO catalyst, and the scope of the reaction have been studied. Finally, reductive heterocyclization using different metals (Pd and Au) supported on MgO has also been performed.Centro de Investigación y Desarrollo en Ciencias Aplicadas2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf8255-8262http://sedici.unlp.edu.ar/handle/10915/104962enginfo:eu-repo/semantics/altIdentifier/issn/2155-5435info:eu-repo/semantics/altIdentifier/doi/10.1021/acscatal.7b01841info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:22:58Zoai:sedici.unlp.edu.ar:10915/104962Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:22:58.972SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
title Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
spellingShingle Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
Marti, L.
Ciencias Exactas
Química
Reductive heterocyclization
2,1-benzisoxazole
Pt/MgO
2-nitroacylarenes
Cascade process
title_short Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
title_full Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
title_fullStr Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
title_full_unstemmed Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
title_sort Chemoselective Reductive Heterocyclization by Controlling the Binomial Architecture of Metal Particles and Acid−Base Properties of the Support
dc.creator.none.fl_str_mv Marti, L.
Sánchez, Laura Mabel
Climent, María J.
Corma, A.
Iborra, S.
Romanelli, Gustavo Pablo
Concepcion, P.
author Marti, L.
author_facet Marti, L.
Sánchez, Laura Mabel
Climent, María J.
Corma, A.
Iborra, S.
Romanelli, Gustavo Pablo
Concepcion, P.
author_role author
author2 Sánchez, Laura Mabel
Climent, María J.
Corma, A.
Iborra, S.
Romanelli, Gustavo Pablo
Concepcion, P.
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Ciencias Exactas
Química
Reductive heterocyclization
2,1-benzisoxazole
Pt/MgO
2-nitroacylarenes
Cascade process
topic Ciencias Exactas
Química
Reductive heterocyclization
2,1-benzisoxazole
Pt/MgO
2-nitroacylarenes
Cascade process
dc.description.none.fl_txt_mv 2,1-Benzisoxazoles have been selectively synthesized through reductive heterocyclization of 2-nitroacylarenes using Pt-supported nanoparticles. The reaction involves a cascade process in which the first step is the reduction of the nitro group into hydroxylamine followed by heterocyclization through the nucleophilic attack of the hydroxylamine group to the carbonyl of the acyl group and further dehydration. The reaction was performed on Pt/C, Pt/TiO₂, and Pt/MgO using hydrogen as the reducing agent under mild reaction conditions. The results showed that Pt/MgO was the most active and selective catalyst. The study of the influence of the crystal size of the metal on the activity and selectivity, combined with the reaction mechanism examined by in situ Fourier transform infrared spectroscopy of the adsorbed reactant, showed that the maximum activity and selectivity to the target compound can be achieved by controlling the architecture of metal particles and acid–base properties of the support. The effect of temperature on selectivity, the stability of the Pt/MgO catalyst, and the scope of the reaction have been studied. Finally, reductive heterocyclization using different metals (Pd and Au) supported on MgO has also been performed.
Centro de Investigación y Desarrollo en Ciencias Aplicadas
description 2,1-Benzisoxazoles have been selectively synthesized through reductive heterocyclization of 2-nitroacylarenes using Pt-supported nanoparticles. The reaction involves a cascade process in which the first step is the reduction of the nitro group into hydroxylamine followed by heterocyclization through the nucleophilic attack of the hydroxylamine group to the carbonyl of the acyl group and further dehydration. The reaction was performed on Pt/C, Pt/TiO₂, and Pt/MgO using hydrogen as the reducing agent under mild reaction conditions. The results showed that Pt/MgO was the most active and selective catalyst. The study of the influence of the crystal size of the metal on the activity and selectivity, combined with the reaction mechanism examined by in situ Fourier transform infrared spectroscopy of the adsorbed reactant, showed that the maximum activity and selectivity to the target compound can be achieved by controlling the architecture of metal particles and acid–base properties of the support. The effect of temperature on selectivity, the stability of the Pt/MgO catalyst, and the scope of the reaction have been studied. Finally, reductive heterocyclization using different metals (Pd and Au) supported on MgO has also been performed.
publishDate 2017
dc.date.none.fl_str_mv 2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/104962
url http://sedici.unlp.edu.ar/handle/10915/104962
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/2155-5435
info:eu-repo/semantics/altIdentifier/doi/10.1021/acscatal.7b01841
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
8255-8262
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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