Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon

Autores
Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalyzed azide-alkyne cycloaddition (CuAAC). High yields of the β-methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the methylsulfanyl group has been demonstrated through a series of synthetic transformations, including direct access to 1-vinyl and 4-monosubstituted triazoles.
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. Universidad de Alicante; España
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
TRIAZOLES
ALKENES
COPPER NANOPARTICLES
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:11336/85826
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbonAlonso, FranciscoMoglie, Yanina FernandaRadivoy, Gabriel EduardoYus, MiguelTRIAZOLESALKENESCOPPER NANOPARTICLEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalyzed azide-alkyne cycloaddition (CuAAC). High yields of the β-methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the methylsulfanyl group has been demonstrated through a series of synthetic transformations, including direct access to 1-vinyl and 4-monosubstituted triazoles.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; Argentina. Universidad de Alicante; EspañaFil: 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 Society2013-05-25info: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/11336/85826Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel; Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon; American Chemical Society; Journal of Organic Chemistry; 78; 10; 25-5-2013; 5031-50370022-3263CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jo400110minfo:eu-repo/semantics/altIdentifier/doi/10.1021/jo400110minfo:eu-repo/semantics/altIdentifier/url/http://rua.ua.es/dspace/handle/10045/28456info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:40:09Zoai:ri.conicet.gov.ar:11336/85826instacron: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:34982025-09-29 09:40:09.544CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon
title Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon
spellingShingle Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon
Alonso, Francisco
TRIAZOLES
ALKENES
COPPER NANOPARTICLES
title_short Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon
title_full Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon
title_fullStr Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon
title_full_unstemmed Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon
title_sort Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles 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 TRIAZOLES
ALKENES
COPPER NANOPARTICLES
topic TRIAZOLES
ALKENES
COPPER NANOPARTICLES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalyzed azide-alkyne cycloaddition (CuAAC). High yields of the β-methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the methylsulfanyl group has been demonstrated through a series of synthetic transformations, including direct access to 1-vinyl and 4-monosubstituted triazoles.
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. Universidad de Alicante; España
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 A one-pot protocol for the synthesis of 1,2,3-triazoles has been developed starting from inactivated alkenes and based on two click reactions: the azidosulfenylation of the carbon-carbon double bond and the copper-catalyzed azide-alkyne cycloaddition (CuAAC). High yields of the β-methylsulfanyl triazoles have been attained using CuNPs/C as catalyst, with other commercial copper catalysts being completely inactive. The versatility of the methylsulfanyl group has been demonstrated through a series of synthetic transformations, including direct access to 1-vinyl and 4-monosubstituted triazoles.
publishDate 2013
dc.date.none.fl_str_mv 2013-05-25
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/11336/85826
Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel; Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon; American Chemical Society; Journal of Organic Chemistry; 78; 10; 25-5-2013; 5031-5037
0022-3263
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85826
identifier_str_mv Alonso, Francisco; Moglie, Yanina Fernanda; Radivoy, Gabriel Eduardo; Yus, Miguel; Alkenes as azido precursors for the one-Pot Synthesis of 1,2,3-triazoles catalyzed by copper nanoparticles on activated carbon; American Chemical Society; Journal of Organic Chemistry; 78; 10; 25-5-2013; 5031-5037
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/10.1021/jo400110m
info:eu-repo/semantics/altIdentifier/doi/10.1021/jo400110m
info:eu-repo/semantics/altIdentifier/url/http://rua.ua.es/dspace/handle/10045/28456
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 13.070432

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