Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation

Autores
Barata Vallejo, Sebastian; Yerien, Damián Emilio; Postigo, Jose Alberto
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, we present a room- or solar-light-initiated transition-metal-free radical homolytic aromatic substitution (HAS) reaction of aniline derivatives with perfluoroalkyl moieties employing perfluoroalkyl halides as readily available perfluoroalkyl sources in the presence of cesium carbonate as base and inexpensive Rose Bengal as organophotocatalyst in MeCN as solvent, rendering perfluoroalkyl-substituted aniline derivatives in good-to-excellent yields, even upon scaling up. Although the mechanism of this reaction is still under investigation, we shall present some evidence based on competitive substitution rate experiments that cast some light onto the reaction intermediates.
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Yerien, Damián Emilio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Perfluoroalkylation
Radical Chemistry
Homolytic Aromatic Substitution
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:11336/15843
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiationBarata Vallejo, SebastianYerien, Damián EmilioPostigo, Jose AlbertoPerfluoroalkylationRadical ChemistryHomolytic Aromatic Substitutionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work, we present a room- or solar-light-initiated transition-metal-free radical homolytic aromatic substitution (HAS) reaction of aniline derivatives with perfluoroalkyl moieties employing perfluoroalkyl halides as readily available perfluoroalkyl sources in the presence of cesium carbonate as base and inexpensive Rose Bengal as organophotocatalyst in MeCN as solvent, rendering perfluoroalkyl-substituted aniline derivatives in good-to-excellent yields, even upon scaling up. Although the mechanism of this reaction is still under investigation, we shall present some evidence based on competitive substitution rate experiments that cast some light onto the reaction intermediates.Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Yerien, Damián Emilio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaWiley VCH Verlag2015-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/15843Barata Vallejo, Sebastian; Yerien, Damián Emilio; Postigo, Jose Alberto; Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 36; 12-2015; 7869-78751434-193X1099-0690enginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201501189info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201501189/fullinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:06:01Zoai:ri.conicet.gov.ar:11336/15843instacron: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 10:06:01.996CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
title Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
spellingShingle Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
Barata Vallejo, Sebastian
Perfluoroalkylation
Radical Chemistry
Homolytic Aromatic Substitution
title_short Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
title_full Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
title_fullStr Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
title_full_unstemmed Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
title_sort Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation
dc.creator.none.fl_str_mv Barata Vallejo, Sebastian
Yerien, Damián Emilio
Postigo, Jose Alberto
author Barata Vallejo, Sebastian
author_facet Barata Vallejo, Sebastian
Yerien, Damián Emilio
Postigo, Jose Alberto
author_role author
author2 Yerien, Damián Emilio
Postigo, Jose Alberto
author2_role author
author
dc.subject.none.fl_str_mv Perfluoroalkylation
Radical Chemistry
Homolytic Aromatic Substitution
topic Perfluoroalkylation
Radical Chemistry
Homolytic Aromatic Substitution
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work, we present a room- or solar-light-initiated transition-metal-free radical homolytic aromatic substitution (HAS) reaction of aniline derivatives with perfluoroalkyl moieties employing perfluoroalkyl halides as readily available perfluoroalkyl sources in the presence of cesium carbonate as base and inexpensive Rose Bengal as organophotocatalyst in MeCN as solvent, rendering perfluoroalkyl-substituted aniline derivatives in good-to-excellent yields, even upon scaling up. Although the mechanism of this reaction is still under investigation, we shall present some evidence based on competitive substitution rate experiments that cast some light onto the reaction intermediates.
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Yerien, Damián Emilio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description In this work, we present a room- or solar-light-initiated transition-metal-free radical homolytic aromatic substitution (HAS) reaction of aniline derivatives with perfluoroalkyl moieties employing perfluoroalkyl halides as readily available perfluoroalkyl sources in the presence of cesium carbonate as base and inexpensive Rose Bengal as organophotocatalyst in MeCN as solvent, rendering perfluoroalkyl-substituted aniline derivatives in good-to-excellent yields, even upon scaling up. Although the mechanism of this reaction is still under investigation, we shall present some evidence based on competitive substitution rate experiments that cast some light onto the reaction intermediates.
publishDate 2015
dc.date.none.fl_str_mv 2015-12
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/11336/15843
Barata Vallejo, Sebastian; Yerien, Damián Emilio; Postigo, Jose Alberto; Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 36; 12-2015; 7869-7875
1434-193X
1099-0690
url http://hdl.handle.net/11336/15843
identifier_str_mv Barata Vallejo, Sebastian; Yerien, Damián Emilio; Postigo, Jose Alberto; Benign perfluoroalkylation of aniline derivatives through photoredox organocatalysis under visible light irradiation; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 36; 12-2015; 7869-7875
1434-193X
1099-0690
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201501189
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201501189/full
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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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