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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/30347
Ver los metadatos del registro completo
id |
CONICETDig_860ed7e86cc12f5c7fcb0ef4b4390db9 |
---|---|
oai_identifier_str |
oai:ri.conicet.gov.ar:11336/30347 |
network_acronym_str |
CONICETDig |
repository_id_str |
3498 |
network_name_str |
CONICET Digital (CONICET) |
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 Técnicas2025-09-29T10:32:03Zoai: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:34982025-09-29 10:32:03.95CONICET 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 |
_version_ |
1844614333159440384 |
score |
13.070432 |