Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents

Autores
Barata Vallejo, Sebastian; Lantaño, Beatriz; Postigo, Jose Alberto
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Electrophilic trifluoromethylation reactions have been the latest approach to achieve the fluoroalkylation of compounds with newly-discovered reagents, such as the Togni’s (1-trifluoromethyl-1,2-benziodoxol-3-(1 H)-one), Umemoto’s (S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate), Yagupolskii’s (S-(trifluoromethyldiarylsulfonium salts), Shreeve’s (S-(trifluoromethyl)dibenzothiophenium triflate), and Shibata’s (trifluoromethylsulfoximine salts) reagents. All these reagents produce an electrophilic trifluoromethylating (CF3+) species that undergoes reaction with nucleophiles. In addition, these latter reactive species (i.e. CF3+) can undergo electron-transfer (ET) processes affording CF3⋅ radicals that expand the scope to substrates other than conventional nucleophiles that can undergo reaction. In this Review, we shall discuss the trifluoromethylation reactions of diverse families of organic substrates of biological interest as a means to comparing the reagents scope and best reaction conditions. Some, though not all, of these reactions require the assistance of metal or organometallic catalysts. Some require additives and catalysts to promote the fluoroalkylation reaction, but invariably all are initiated and carried out by electrophilic trifluoromethylating species.
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: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; 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
Electrophilic Addition
Fluorinated Compounds
Radical Reactions
Synthetic 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:11336/30347
Acceder
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spelling Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating ReagentsBarata Vallejo, SebastianLantaño, BeatrizPostigo, Jose AlbertoElectrophilic AdditionFluorinated CompoundsRadical ReactionsSynthetic Methodshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Electrophilic trifluoromethylation reactions have been the latest approach to achieve the fluoroalkylation of compounds with newly-discovered reagents, such as the Togni’s (1-trifluoromethyl-1,2-benziodoxol-3-(1 H)-one), Umemoto’s (S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate), Yagupolskii’s (S-(trifluoromethyldiarylsulfonium salts), Shreeve’s (S-(trifluoromethyl)dibenzothiophenium triflate), and Shibata’s (trifluoromethylsulfoximine salts) reagents. All these reagents produce an electrophilic trifluoromethylating (CF3+) species that undergoes reaction with nucleophiles. In addition, these latter reactive species (i.e. CF3+) can undergo electron-transfer (ET) processes affording CF3⋅ radicals that expand the scope to substrates other than conventional nucleophiles that can undergo reaction. In this Review, we shall discuss the trifluoromethylation reactions of diverse families of organic substrates of biological interest as a means to comparing the reagents scope and best reaction conditions. Some, though not all, of these reactions require the assistance of metal or organometallic catalysts. Some require additives and catalysts to promote the fluoroalkylation reaction, but invariably all are initiated and carried out by electrophilic trifluoromethylating species.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: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; 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; ArgentinaWiley2014-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/30347Barata Vallejo, Sebastian; Lantaño, Beatriz; Postigo, Jose Alberto; Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents; Wiley; Chemistry A European journal; 20; 51; 10-2014; 16806-168291521-37651521-3765CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201404005info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.201404005/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:04:29Zoai:ri.conicet.gov.ar:11336/30347instacron: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 12:04:29.441CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
title Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
spellingShingle Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
Barata Vallejo, Sebastian
Electrophilic Addition
Fluorinated Compounds
Radical Reactions
Synthetic Methods
title_short Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
title_full Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
title_fullStr Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
title_full_unstemmed Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
title_sort Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents
dc.creator.none.fl_str_mv Barata Vallejo, Sebastian
Lantaño, Beatriz
Postigo, Jose Alberto
author Barata Vallejo, Sebastian
author_facet Barata Vallejo, Sebastian
Lantaño, Beatriz
Postigo, Jose Alberto
author_role author
author2 Lantaño, Beatriz
Postigo, Jose Alberto
author2_role author
author
dc.subject.none.fl_str_mv Electrophilic Addition
Fluorinated Compounds
Radical Reactions
Synthetic Methods
topic Electrophilic Addition
Fluorinated Compounds
Radical Reactions
Synthetic 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 Electrophilic trifluoromethylation reactions have been the latest approach to achieve the fluoroalkylation of compounds with newly-discovered reagents, such as the Togni’s (1-trifluoromethyl-1,2-benziodoxol-3-(1 H)-one), Umemoto’s (S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate), Yagupolskii’s (S-(trifluoromethyldiarylsulfonium salts), Shreeve’s (S-(trifluoromethyl)dibenzothiophenium triflate), and Shibata’s (trifluoromethylsulfoximine salts) reagents. All these reagents produce an electrophilic trifluoromethylating (CF3+) species that undergoes reaction with nucleophiles. In addition, these latter reactive species (i.e. CF3+) can undergo electron-transfer (ET) processes affording CF3⋅ radicals that expand the scope to substrates other than conventional nucleophiles that can undergo reaction. In this Review, we shall discuss the trifluoromethylation reactions of diverse families of organic substrates of biological interest as a means to comparing the reagents scope and best reaction conditions. Some, though not all, of these reactions require the assistance of metal or organometallic catalysts. Some require additives and catalysts to promote the fluoroalkylation reaction, but invariably all are initiated and carried out by electrophilic trifluoromethylating species.
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: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; 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 Electrophilic trifluoromethylation reactions have been the latest approach to achieve the fluoroalkylation of compounds with newly-discovered reagents, such as the Togni’s (1-trifluoromethyl-1,2-benziodoxol-3-(1 H)-one), Umemoto’s (S-(trifluoromethyl)dibenzothiophenium tetrafluoroborate), Yagupolskii’s (S-(trifluoromethyldiarylsulfonium salts), Shreeve’s (S-(trifluoromethyl)dibenzothiophenium triflate), and Shibata’s (trifluoromethylsulfoximine salts) reagents. All these reagents produce an electrophilic trifluoromethylating (CF3+) species that undergoes reaction with nucleophiles. In addition, these latter reactive species (i.e. CF3+) can undergo electron-transfer (ET) processes affording CF3⋅ radicals that expand the scope to substrates other than conventional nucleophiles that can undergo reaction. In this Review, we shall discuss the trifluoromethylation reactions of diverse families of organic substrates of biological interest as a means to comparing the reagents scope and best reaction conditions. Some, though not all, of these reactions require the assistance of metal or organometallic catalysts. Some require additives and catalysts to promote the fluoroalkylation reaction, but invariably all are initiated and carried out by electrophilic trifluoromethylating species.
publishDate 2014
dc.date.none.fl_str_mv 2014-10
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/11336/30347
Barata Vallejo, Sebastian; Lantaño, Beatriz; Postigo, Jose Alberto; Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents; Wiley; Chemistry A European journal; 20; 51; 10-2014; 16806-16829
1521-3765
1521-3765
CONICET Digital
CONICET
url http://hdl.handle.net/11336/30347
identifier_str_mv Barata Vallejo, Sebastian; Lantaño, Beatriz; Postigo, Jose Alberto; Recent Advances in Trifluoromethylation Reactions with Electrophilic Trifluoromethylating Reagents; Wiley; Chemistry A European journal; 20; 51; 10-2014; 16806-16829
1521-3765
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/chem.201404005
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chem.201404005/abstract
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
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
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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