Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes

Autores
Yerien, Damián Emilio; Lantaño, Beatriz; Barata Vallejo, Sebastian; Postigo, Jose Alberto
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Electron-rich alcoxy-substituted (hetero)arenes and electrophilic fluoroalkyl moieties represent advantageous partners for substitution reactions due to their electronic match. Fluoroalkylation strategies of alcoxy-substituted (hetero)arenes are herein presented which depict photocatalytic and thermal methods. Photocatalytic methods rely on the use of diverse photocatalysts such as Ru(bpy)3Cl2, tetrabutylammonium decatungstate TBADT, N-doped carbon nanodots NCNDs, and vitamin derivatives which can partner with the Langlois reagent NaSO2CF3, CF3CO2H, and perfluoroalkyl iodides RFI as fluoroalkylating reagents. Also, electrocatalytic methods that make use of the cathodic reduction of CF3SO2Cl to generate CF3 radicals can achieve trifluoromethylation reactions of alcoxysubstituted (hetero)arenes. On the other hand, thermal methodologies comprising Pd(OAc)2 catalysis and using CF3Br as trifluoromethylating source have been implemented.
Fil: Yerien, Damián Emilio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consiglio Nazionale delle Ricerche; Italia
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina
Materia
ALKOXY-SUBSTITUTED (HETERO)ARENES
ELECTROCHEMICAL FLUOROALKYLATION METHODS
FLUOROALKYLATION STRATEGIES
PHOTOCATALYTIC FLUOROALKYLATION
RADICAL FLUOROALKYLATION METHODS
THERMAL FLUOROALKYLATION METHODS
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:11336/150046
Acceder
id CONICETDig_40ac8f16b251d39939c363e39acce155
oai_identifier_str oai:ri.conicet.gov.ar:11336/150046
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)ArenesYerien, Damián EmilioLantaño, BeatrizBarata Vallejo, SebastianPostigo, Jose AlbertoALKOXY-SUBSTITUTED (HETERO)ARENESELECTROCHEMICAL FLUOROALKYLATION METHODSFLUOROALKYLATION STRATEGIESPHOTOCATALYTIC FLUOROALKYLATIONRADICAL FLUOROALKYLATION METHODSTHERMAL FLUOROALKYLATION METHODShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Electron-rich alcoxy-substituted (hetero)arenes and electrophilic fluoroalkyl moieties represent advantageous partners for substitution reactions due to their electronic match. Fluoroalkylation strategies of alcoxy-substituted (hetero)arenes are herein presented which depict photocatalytic and thermal methods. Photocatalytic methods rely on the use of diverse photocatalysts such as Ru(bpy)3Cl2, tetrabutylammonium decatungstate TBADT, N-doped carbon nanodots NCNDs, and vitamin derivatives which can partner with the Langlois reagent NaSO2CF3, CF3CO2H, and perfluoroalkyl iodides RFI as fluoroalkylating reagents. Also, electrocatalytic methods that make use of the cathodic reduction of CF3SO2Cl to generate CF3 radicals can achieve trifluoromethylation reactions of alcoxysubstituted (hetero)arenes. On the other hand, thermal methodologies comprising Pd(OAc)2 catalysis and using CF3Br as trifluoromethylating source have been implemented.Fil: Yerien, Damián Emilio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; ArgentinaFil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consiglio Nazionale delle Ricerche; ItaliaFil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; ArgentinaWiley VCH Verlag2021-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/150046Yerien, Damián Emilio; Lantaño, Beatriz; Barata Vallejo, Sebastian; Postigo, Jose Alberto; Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes; Wiley VCH Verlag; Chemcatchem; 13; 21; 11-2021; 4497-45061867-3880CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/10.1002/cctc.202100997info:eu-repo/semantics/altIdentifier/doi/10.1002/cctc.202100997info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:05:38Zoai:ri.conicet.gov.ar:11336/150046instacron: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 10:05:38.758CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
title Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
spellingShingle Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
Yerien, Damián Emilio
ALKOXY-SUBSTITUTED (HETERO)ARENES
ELECTROCHEMICAL FLUOROALKYLATION METHODS
FLUOROALKYLATION STRATEGIES
PHOTOCATALYTIC FLUOROALKYLATION
RADICAL FLUOROALKYLATION METHODS
THERMAL FLUOROALKYLATION METHODS
title_short Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
title_full Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
title_fullStr Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
title_full_unstemmed Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
title_sort Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes
dc.creator.none.fl_str_mv Yerien, Damián Emilio
Lantaño, Beatriz
Barata Vallejo, Sebastian
Postigo, Jose Alberto
author Yerien, Damián Emilio
author_facet Yerien, Damián Emilio
Lantaño, Beatriz
Barata Vallejo, Sebastian
Postigo, Jose Alberto
author_role author
author2 Lantaño, Beatriz
Barata Vallejo, Sebastian
Postigo, Jose Alberto
author2_role author
author
author
dc.subject.none.fl_str_mv ALKOXY-SUBSTITUTED (HETERO)ARENES
ELECTROCHEMICAL FLUOROALKYLATION METHODS
FLUOROALKYLATION STRATEGIES
PHOTOCATALYTIC FLUOROALKYLATION
RADICAL FLUOROALKYLATION METHODS
THERMAL FLUOROALKYLATION METHODS
topic ALKOXY-SUBSTITUTED (HETERO)ARENES
ELECTROCHEMICAL FLUOROALKYLATION METHODS
FLUOROALKYLATION STRATEGIES
PHOTOCATALYTIC FLUOROALKYLATION
RADICAL FLUOROALKYLATION METHODS
THERMAL FLUOROALKYLATION METHODS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Electron-rich alcoxy-substituted (hetero)arenes and electrophilic fluoroalkyl moieties represent advantageous partners for substitution reactions due to their electronic match. Fluoroalkylation strategies of alcoxy-substituted (hetero)arenes are herein presented which depict photocatalytic and thermal methods. Photocatalytic methods rely on the use of diverse photocatalysts such as Ru(bpy)3Cl2, tetrabutylammonium decatungstate TBADT, N-doped carbon nanodots NCNDs, and vitamin derivatives which can partner with the Langlois reagent NaSO2CF3, CF3CO2H, and perfluoroalkyl iodides RFI as fluoroalkylating reagents. Also, electrocatalytic methods that make use of the cathodic reduction of CF3SO2Cl to generate CF3 radicals can achieve trifluoromethylation reactions of alcoxysubstituted (hetero)arenes. On the other hand, thermal methodologies comprising Pd(OAc)2 catalysis and using CF3Br as trifluoromethylating source have been implemented.
Fil: Yerien, Damián Emilio. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina. Consiglio Nazionale delle Ricerche; Italia
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; Argentina
description Electron-rich alcoxy-substituted (hetero)arenes and electrophilic fluoroalkyl moieties represent advantageous partners for substitution reactions due to their electronic match. Fluoroalkylation strategies of alcoxy-substituted (hetero)arenes are herein presented which depict photocatalytic and thermal methods. Photocatalytic methods rely on the use of diverse photocatalysts such as Ru(bpy)3Cl2, tetrabutylammonium decatungstate TBADT, N-doped carbon nanodots NCNDs, and vitamin derivatives which can partner with the Langlois reagent NaSO2CF3, CF3CO2H, and perfluoroalkyl iodides RFI as fluoroalkylating reagents. Also, electrocatalytic methods that make use of the cathodic reduction of CF3SO2Cl to generate CF3 radicals can achieve trifluoromethylation reactions of alcoxysubstituted (hetero)arenes. On the other hand, thermal methodologies comprising Pd(OAc)2 catalysis and using CF3Br as trifluoromethylating source have been implemented.
publishDate 2021
dc.date.none.fl_str_mv 2021-11
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/11336/150046
Yerien, Damián Emilio; Lantaño, Beatriz; Barata Vallejo, Sebastian; Postigo, Jose Alberto; Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes; Wiley VCH Verlag; Chemcatchem; 13; 21; 11-2021; 4497-4506
1867-3880
CONICET Digital
CONICET
url http://hdl.handle.net/11336/150046
identifier_str_mv Yerien, Damián Emilio; Lantaño, Beatriz; Barata Vallejo, Sebastian; Postigo, Jose Alberto; Catalytic Fluoroalkylation Reactions of Alcoxy‐subtituted (Hetero)Arenes; Wiley VCH Verlag; Chemcatchem; 13; 21; 11-2021; 4497-4506
1867-3880
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://onlinelibrary.wiley.com/doi/10.1002/cctc.202100997
info:eu-repo/semantics/altIdentifier/doi/10.1002/cctc.202100997
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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