Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon

Autores
Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Copper nanoparticles on activated carbon have been found to effectively catalyze the multicomponent synthesis of β-hydroxy-1,2,3-triazoles from a variety of epoxides and alkynes in water. The catalyst is easy to prepare, reusable at a low copper loading (0.5 mol %), and exhibits higher catalytic activity than some commercially available copper sources. The regio- and stereochemistry of the reaction has been revised and unequivocally established on the basis of X-ray crystallographic analyses. An NMR experiment has been implemented for the rapid and unmistakable determination of the regiochemistry of the process. Some mechanistic aspects of the reaction have been also undertaken which unveil the participation of copper(I) acetylides.
Fil: Alonso, Francisco. Universidad de Alicante; España
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: 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
Fil: Yus, Miguel. Universidad de Alicante; España
Materia
CLICK CHEMISTRY
EPOXIDES
TRIAZOLES
COPPER NANOPARTICLES
REGIOSELECTIVITY
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:11336/157179
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated CarbonAlonso, FranciscoMoglie, Yanina FernandaRadivoy, Gabriel EduardoYus, MiguelCLICK CHEMISTRYEPOXIDESTRIAZOLESCOPPER NANOPARTICLESREGIOSELECTIVITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Copper nanoparticles on activated carbon have been found to effectively catalyze the multicomponent synthesis of β-hydroxy-1,2,3-triazoles from a variety of epoxides and alkynes in water. The catalyst is easy to prepare, reusable at a low copper loading (0.5 mol %), and exhibits higher catalytic activity than some commercially available copper sources. The regio- and stereochemistry of the reaction has been revised and unequivocally established on the basis of X-ray crystallographic analyses. An NMR experiment has been implemented for the rapid and unmistakable determination of the regiochemistry of the process. Some mechanistic aspects of the reaction have been also undertaken which unveil the participation of copper(I) acetylides.Fil: Alonso, Francisco. Universidad de Alicante; EspañaFil: 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: 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; ArgentinaFil: Yus, Miguel. Universidad de Alicante; EspañaAmerican Chemical Society2011-09-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/157179Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel; Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon; American Chemical Society; Journal of Organic Chemistry; 76; 20; 6-9-2011; 8394-84050022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jo2016339info:eu-repo/semantics/altIdentifier/doi/10.1021/jo2016339info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:43:52Zoai:ri.conicet.gov.ar:11336/157179instacron: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:34982025-09-03 09:43:52.385CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
title Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
spellingShingle Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
Alonso, Francisco
CLICK CHEMISTRY
EPOXIDES
TRIAZOLES
COPPER NANOPARTICLES
REGIOSELECTIVITY
title_short Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
title_full Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
title_fullStr Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
title_full_unstemmed Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
title_sort Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon
dc.creator.none.fl_str_mv Alonso, Francisco
Moglie, Yanina Fernanda
Radivoy, Gabriel Eduardo
Yus, Miguel
author Alonso, Francisco
author_facet Alonso, Francisco
Moglie, Yanina Fernanda
Radivoy, Gabriel Eduardo
Yus, Miguel
author_role author
author2 Moglie, Yanina Fernanda
Radivoy, Gabriel Eduardo
Yus, Miguel
author2_role author
author
author
dc.subject.none.fl_str_mv CLICK CHEMISTRY
EPOXIDES
TRIAZOLES
COPPER NANOPARTICLES
REGIOSELECTIVITY
topic CLICK CHEMISTRY
EPOXIDES
TRIAZOLES
COPPER NANOPARTICLES
REGIOSELECTIVITY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Copper nanoparticles on activated carbon have been found to effectively catalyze the multicomponent synthesis of β-hydroxy-1,2,3-triazoles from a variety of epoxides and alkynes in water. The catalyst is easy to prepare, reusable at a low copper loading (0.5 mol %), and exhibits higher catalytic activity than some commercially available copper sources. The regio- and stereochemistry of the reaction has been revised and unequivocally established on the basis of X-ray crystallographic analyses. An NMR experiment has been implemented for the rapid and unmistakable determination of the regiochemistry of the process. Some mechanistic aspects of the reaction have been also undertaken which unveil the participation of copper(I) acetylides.
Fil: Alonso, Francisco. Universidad de Alicante; España
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: 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
Fil: Yus, Miguel. Universidad de Alicante; España
description Copper nanoparticles on activated carbon have been found to effectively catalyze the multicomponent synthesis of β-hydroxy-1,2,3-triazoles from a variety of epoxides and alkynes in water. The catalyst is easy to prepare, reusable at a low copper loading (0.5 mol %), and exhibits higher catalytic activity than some commercially available copper sources. The regio- and stereochemistry of the reaction has been revised and unequivocally established on the basis of X-ray crystallographic analyses. An NMR experiment has been implemented for the rapid and unmistakable determination of the regiochemistry of the process. Some mechanistic aspects of the reaction have been also undertaken which unveil the participation of copper(I) acetylides.
publishDate 2011
dc.date.none.fl_str_mv 2011-09-06
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/11336/157179
Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel; Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon; American Chemical Society; Journal of Organic Chemistry; 76; 20; 6-9-2011; 8394-8405
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/157179
identifier_str_mv Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel; Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbon; American Chemical Society; Journal of Organic Chemistry; 76; 20; 6-9-2011; 8394-8405
0022-3263
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jo2016339
info:eu-repo/semantics/altIdentifier/doi/10.1021/jo2016339
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
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 13.13397

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