Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles

Autores
Solé, Daniel; Pérez Janer, Ferran; Zulaica, Ester; Guastavino, Javier Fernando; Fernádez, Israel
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A novel four-step domino process for the synthesis of 3-[2-(aryl/alkylsulfonyl)ethyl]indoles starting from readily available 2-iodoanilines is reported. The domino reaction is based on the intramolecular palladium-catalyzed α-arylation of sulfones, which was combined with both intermolecular aza-Michael and Michael addition reactions using vinyl sulfones as the electrophile. The domino process produced good yields and tolerated the presence of substituents with different electronic properties on the aniline ring. In addition, density functional theory (DFT) calculations were carried out to gain more insight into the formation of the observed indole derivatives
Fil: Solé, Daniel. Universidad de Barcelona; España
Fil: Pérez Janer, Ferran. Universidad de Barcelona; España
Fil: Zulaica, Ester. Universidad de Barcelona; España
Fil: Guastavino, Javier Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Fernádez, Israel. Universidad de Barcelona; España. Universidad Complutense de Madrid; España
Materia
palladium-catalyzed
arylation
domino reactions
indoles
density functional calculations
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:11336/19491
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/19491
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indolesSolé, DanielPérez Janer, FerranZulaica, EsterGuastavino, Javier FernandoFernádez, Israelpalladium-catalyzedarylationdomino reactionsindolesdensity functional calculationshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A novel four-step domino process for the synthesis of 3-[2-(aryl/alkylsulfonyl)ethyl]indoles starting from readily available 2-iodoanilines is reported. The domino reaction is based on the intramolecular palladium-catalyzed α-arylation of sulfones, which was combined with both intermolecular aza-Michael and Michael addition reactions using vinyl sulfones as the electrophile. The domino process produced good yields and tolerated the presence of substituents with different electronic properties on the aniline ring. In addition, density functional theory (DFT) calculations were carried out to gain more insight into the formation of the observed indole derivativesFil: Solé, Daniel. Universidad de Barcelona; EspañaFil: Pérez Janer, Ferran. Universidad de Barcelona; EspañaFil: Zulaica, Ester. Universidad de Barcelona; EspañaFil: Guastavino, Javier Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaFil: Fernádez, Israel. Universidad de Barcelona; España. Universidad Complutense de Madrid; EspañaAmerican Chemical Society2016-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/19491Solé, Daniel; Pérez Janer, Ferran; Zulaica, Ester; Guastavino, Javier Fernando; Fernádez, Israel; Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles; American Chemical Society; ACS Catalysis; 6; 3; 2-2016; 1691-17002155-5435CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acscatal.6b00027info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/acscatal.6b00027info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:56:08Zoai:ri.conicet.gov.ar:11336/19491instacron: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:34982025-10-22 11:56:08.33CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
title Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
spellingShingle Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
Solé, Daniel
palladium-catalyzed
arylation
domino reactions
indoles
density functional calculations
title_short Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
title_full Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
title_fullStr Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
title_full_unstemmed Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
title_sort Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles
dc.creator.none.fl_str_mv Solé, Daniel
Pérez Janer, Ferran
Zulaica, Ester
Guastavino, Javier Fernando
Fernádez, Israel
author Solé, Daniel
author_facet Solé, Daniel
Pérez Janer, Ferran
Zulaica, Ester
Guastavino, Javier Fernando
Fernádez, Israel
author_role author
author2 Pérez Janer, Ferran
Zulaica, Ester
Guastavino, Javier Fernando
Fernádez, Israel
author2_role author
author
author
author
dc.subject.none.fl_str_mv palladium-catalyzed
arylation
domino reactions
indoles
density functional calculations
topic palladium-catalyzed
arylation
domino reactions
indoles
density functional calculations
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 novel four-step domino process for the synthesis of 3-[2-(aryl/alkylsulfonyl)ethyl]indoles starting from readily available 2-iodoanilines is reported. The domino reaction is based on the intramolecular palladium-catalyzed α-arylation of sulfones, which was combined with both intermolecular aza-Michael and Michael addition reactions using vinyl sulfones as the electrophile. The domino process produced good yields and tolerated the presence of substituents with different electronic properties on the aniline ring. In addition, density functional theory (DFT) calculations were carried out to gain more insight into the formation of the observed indole derivatives
Fil: Solé, Daniel. Universidad de Barcelona; España
Fil: Pérez Janer, Ferran. Universidad de Barcelona; España
Fil: Zulaica, Ester. Universidad de Barcelona; España
Fil: Guastavino, Javier Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Fernádez, Israel. Universidad de Barcelona; España. Universidad Complutense de Madrid; España
description A novel four-step domino process for the synthesis of 3-[2-(aryl/alkylsulfonyl)ethyl]indoles starting from readily available 2-iodoanilines is reported. The domino reaction is based on the intramolecular palladium-catalyzed α-arylation of sulfones, which was combined with both intermolecular aza-Michael and Michael addition reactions using vinyl sulfones as the electrophile. The domino process produced good yields and tolerated the presence of substituents with different electronic properties on the aniline ring. In addition, density functional theory (DFT) calculations were carried out to gain more insight into the formation of the observed indole derivatives
publishDate 2016
dc.date.none.fl_str_mv 2016-02
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/11336/19491
Solé, Daniel; Pérez Janer, Ferran; Zulaica, Ester; Guastavino, Javier Fernando; Fernádez, Israel; Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles; American Chemical Society; ACS Catalysis; 6; 3; 2-2016; 1691-1700
2155-5435
CONICET Digital
CONICET
url http://hdl.handle.net/11336/19491
identifier_str_mv Solé, Daniel; Pérez Janer, Ferran; Zulaica, Ester; Guastavino, Javier Fernando; Fernádez, Israel; Pd-Catalyzed alfa-Arylation of Sulfones in a Three-Component Synthesis 3-[2-(phenyl/methylsulfonyl)ethyl]indoles; American Chemical Society; ACS Catalysis; 6; 3; 2-2016; 1691-1700
2155-5435
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acscatal.6b00027
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/acscatal.6b00027
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
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
_version_ 1846782266687094784
score 12.982451

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