Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism

Autores
Fortunato, Leandro Federico; Moglie, Yanina Fernanda; Dorn, Viviana; Radivoy, Gabriel Eduardo
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The reaction mechanism of the CuNPs/ZnO-catalyzed hydrophosphorylation of aliphatic alkynes for the synthesis of vinyl phosphonates has been investigated. Based on experimental observations and theoretical calculations through DFT studies, a reaction mechanism is proposed, in which a crucial role of both the solvent and the catalyst support is suggested. DFT studies and experimental data, are consistent with a reaction mechanism based on a copper-catalyzed anti-Markovnikov hydrophosphorylation process that favours the formation of the vinyl phosphonate E isomer.
Fil: Fortunato, Leandro Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Moglie, Yanina Fernanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Dorn, Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Radivoy, Gabriel Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Materia
HYDROPHOSPHORYLATION
SUPPORTED COPPER NANOPARTICLES
VINYL PHOSPHONATES
DFT STUDY
HYDROPHOSPHORYLATION
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/55846
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanismFortunato, Leandro FedericoMoglie, Yanina FernandaDorn, VivianaRadivoy, Gabriel EduardoHYDROPHOSPHORYLATIONSUPPORTED COPPER NANOPARTICLESVINYL PHOSPHONATESDFT STUDYHYDROPHOSPHORYLATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The reaction mechanism of the CuNPs/ZnO-catalyzed hydrophosphorylation of aliphatic alkynes for the synthesis of vinyl phosphonates has been investigated. Based on experimental observations and theoretical calculations through DFT studies, a reaction mechanism is proposed, in which a crucial role of both the solvent and the catalyst support is suggested. DFT studies and experimental data, are consistent with a reaction mechanism based on a copper-catalyzed anti-Markovnikov hydrophosphorylation process that favours the formation of the vinyl phosphonate E isomer.Fil: Fortunato, Leandro Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Moglie, Yanina Fernanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Dorn, Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Radivoy, Gabriel Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaRoyal Society of Chemistry2017-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/55846Fortunato, Leandro Federico; Moglie, Yanina Fernanda; Dorn, Viviana; Radivoy, Gabriel Eduardo; Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism; Royal Society of Chemistry; RSC Advances; 7; 30; 3-2017; 18707-187132046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c7ra01037kinfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/RA/C7RA01037Kinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:45:02Zoai:ri.conicet.gov.ar:11336/55846instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-12 09:45:02.337CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
title Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
spellingShingle Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
Fortunato, Leandro Federico
HYDROPHOSPHORYLATION
SUPPORTED COPPER NANOPARTICLES
VINYL PHOSPHONATES
DFT STUDY
HYDROPHOSPHORYLATION
title_short Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
title_full Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
title_fullStr Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
title_full_unstemmed Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
title_sort Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism
dc.creator.none.fl_str_mv Fortunato, Leandro Federico
Moglie, Yanina Fernanda
Dorn, Viviana
Radivoy, Gabriel Eduardo
author Fortunato, Leandro Federico
author_facet Fortunato, Leandro Federico
Moglie, Yanina Fernanda
Dorn, Viviana
Radivoy, Gabriel Eduardo
author_role author
author2 Moglie, Yanina Fernanda
Dorn, Viviana
Radivoy, Gabriel Eduardo
author2_role author
author
author
dc.subject.none.fl_str_mv HYDROPHOSPHORYLATION
SUPPORTED COPPER NANOPARTICLES
VINYL PHOSPHONATES
DFT STUDY
HYDROPHOSPHORYLATION
topic HYDROPHOSPHORYLATION
SUPPORTED COPPER NANOPARTICLES
VINYL PHOSPHONATES
DFT STUDY
HYDROPHOSPHORYLATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The reaction mechanism of the CuNPs/ZnO-catalyzed hydrophosphorylation of aliphatic alkynes for the synthesis of vinyl phosphonates has been investigated. Based on experimental observations and theoretical calculations through DFT studies, a reaction mechanism is proposed, in which a crucial role of both the solvent and the catalyst support is suggested. DFT studies and experimental data, are consistent with a reaction mechanism based on a copper-catalyzed anti-Markovnikov hydrophosphorylation process that favours the formation of the vinyl phosphonate E isomer.
Fil: Fortunato, Leandro Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Moglie, Yanina Fernanda. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Dorn, Viviana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Radivoy, Gabriel Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
description The reaction mechanism of the CuNPs/ZnO-catalyzed hydrophosphorylation of aliphatic alkynes for the synthesis of vinyl phosphonates has been investigated. Based on experimental observations and theoretical calculations through DFT studies, a reaction mechanism is proposed, in which a crucial role of both the solvent and the catalyst support is suggested. DFT studies and experimental data, are consistent with a reaction mechanism based on a copper-catalyzed anti-Markovnikov hydrophosphorylation process that favours the formation of the vinyl phosphonate E isomer.
publishDate 2017
dc.date.none.fl_str_mv 2017-03
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
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://hdl.handle.net/11336/55846
Fortunato, Leandro Federico; Moglie, Yanina Fernanda; Dorn, Viviana; Radivoy, Gabriel Eduardo; Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism; Royal Society of Chemistry; RSC Advances; 7; 30; 3-2017; 18707-18713
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/55846
identifier_str_mv Fortunato, Leandro Federico; Moglie, Yanina Fernanda; Dorn, Viviana; Radivoy, Gabriel Eduardo; Hydrophosphorylation of aliphatic alkynes catalyzed by CuNPs/ZnO for the synthesis of vinyl phosphonates: a DFT study on the reaction mechanism; Royal Society of Chemistry; RSC Advances; 7; 30; 3-2017; 18707-18713
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c7ra01037k
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/RA/C7RA01037K
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.976206

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