Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates

Autores
Barata Vallejo, Sebastian; Yerien, Damián Emilio; Zottola, Agustín Ariel; Postigo, Jose Alberto
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The direct addition of perfluoroacyl (-CORF) groups to organic frameworks has seen a resurgence in interest due to the benefits of these groups in late-stage modification of pro-drugs and biologically active compounds, helping to identify new active leads. The presence of -CORF groups positively impacts the structure- activity relationships of these compounds. In that sense, both polar methods and radical protocols have been developed for the direct syntheses of trifluoromethyl and perfluoroalkyl ketones. In particular, methodologies to tame the unstable trifluoroacyl radical, which could be a key intermediate in the late-stage syntheses of trifluoroacyl- substituted compounds, has allowed much progress in this area. In the next sections, the direct incorporation of perfluoroacyl groups into (hetero)aromatic compounds, -CORF substitutions at Csp3-H, alkyl halides, alkenes, amides, and N-atoms will be discussed in detail, suggesting the future directions and perspectives in the field. These known reactions are summarized in Table 1.
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Yerien, Damián Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina
Fil: Zottola, Agustín Ariel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina
Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Materia
perfluoroacylation
trifluoroacetylation
perfluoroalkyl ketones
perfluoroalkyl (hetero)aryl
Nivel de accesibilidad
acceso embargado
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:11336/247287
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic SubstratesBarata Vallejo, SebastianYerien, Damián EmilioZottola, Agustín ArielPostigo, Jose Albertoperfluoroacylationtrifluoroacetylationperfluoroalkyl ketonesperfluoroalkyl (hetero)arylhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The direct addition of perfluoroacyl (-CORF) groups to organic frameworks has seen a resurgence in interest due to the benefits of these groups in late-stage modification of pro-drugs and biologically active compounds, helping to identify new active leads. The presence of -CORF groups positively impacts the structure- activity relationships of these compounds. In that sense, both polar methods and radical protocols have been developed for the direct syntheses of trifluoromethyl and perfluoroalkyl ketones. In particular, methodologies to tame the unstable trifluoroacyl radical, which could be a key intermediate in the late-stage syntheses of trifluoroacyl- substituted compounds, has allowed much progress in this area. In the next sections, the direct incorporation of perfluoroacyl groups into (hetero)aromatic compounds, -CORF substitutions at Csp3-H, alkyl halides, alkenes, amides, and N-atoms will be discussed in detail, suggesting the future directions and perspectives in the field. These known reactions are summarized in Table 1.Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Yerien, Damián Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; ArgentinaFil: Zottola, Agustín Ariel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; ArgentinaFil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaWiley VCH Verlag2024-10info:eu-repo/date/embargoEnd/2025-03-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/247287Barata Vallejo, Sebastian; Yerien, Damián Emilio; Zottola, Agustín Ariel; Postigo, Jose Alberto; Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates; Wiley VCH Verlag; European Journal of Organic Chemistry; 10-2024; 1-181434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202400898info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202400898info:eu-repo/semantics/embargoedAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:26:15Zoai:ri.conicet.gov.ar:11336/247287instacron: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:34982025-10-15 14:26:16.094CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
title Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
spellingShingle Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
Barata Vallejo, Sebastian
perfluoroacylation
trifluoroacetylation
perfluoroalkyl ketones
perfluoroalkyl (hetero)aryl
title_short Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
title_full Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
title_fullStr Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
title_full_unstemmed Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
title_sort Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates
dc.creator.none.fl_str_mv Barata Vallejo, Sebastian
Yerien, Damián Emilio
Zottola, Agustín Ariel
Postigo, Jose Alberto
author Barata Vallejo, Sebastian
author_facet Barata Vallejo, Sebastian
Yerien, Damián Emilio
Zottola, Agustín Ariel
Postigo, Jose Alberto
author_role author
author2 Yerien, Damián Emilio
Zottola, Agustín Ariel
Postigo, Jose Alberto
author2_role author
author
author
dc.subject.none.fl_str_mv perfluoroacylation
trifluoroacetylation
perfluoroalkyl ketones
perfluoroalkyl (hetero)aryl
topic perfluoroacylation
trifluoroacetylation
perfluoroalkyl ketones
perfluoroalkyl (hetero)aryl
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The direct addition of perfluoroacyl (-CORF) groups to organic frameworks has seen a resurgence in interest due to the benefits of these groups in late-stage modification of pro-drugs and biologically active compounds, helping to identify new active leads. The presence of -CORF groups positively impacts the structure- activity relationships of these compounds. In that sense, both polar methods and radical protocols have been developed for the direct syntheses of trifluoromethyl and perfluoroalkyl ketones. In particular, methodologies to tame the unstable trifluoroacyl radical, which could be a key intermediate in the late-stage syntheses of trifluoroacyl- substituted compounds, has allowed much progress in this area. In the next sections, the direct incorporation of perfluoroacyl groups into (hetero)aromatic compounds, -CORF substitutions at Csp3-H, alkyl halides, alkenes, amides, and N-atoms will be discussed in detail, suggesting the future directions and perspectives in the field. These known reactions are summarized in Table 1.
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
Fil: Yerien, Damián Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina
Fil: Zottola, Agustín Ariel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina
Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Cátedra de Química Orgánica I; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; Argentina
description The direct addition of perfluoroacyl (-CORF) groups to organic frameworks has seen a resurgence in interest due to the benefits of these groups in late-stage modification of pro-drugs and biologically active compounds, helping to identify new active leads. The presence of -CORF groups positively impacts the structure- activity relationships of these compounds. In that sense, both polar methods and radical protocols have been developed for the direct syntheses of trifluoromethyl and perfluoroalkyl ketones. In particular, methodologies to tame the unstable trifluoroacyl radical, which could be a key intermediate in the late-stage syntheses of trifluoroacyl- substituted compounds, has allowed much progress in this area. In the next sections, the direct incorporation of perfluoroacyl groups into (hetero)aromatic compounds, -CORF substitutions at Csp3-H, alkyl halides, alkenes, amides, and N-atoms will be discussed in detail, suggesting the future directions and perspectives in the field. These known reactions are summarized in Table 1.
publishDate 2024
dc.date.none.fl_str_mv 2024-10
info:eu-repo/date/embargoEnd/2025-03-05
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/11336/247287
Barata Vallejo, Sebastian; Yerien, Damián Emilio; Zottola, Agustín Ariel; Postigo, Jose Alberto; Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates; Wiley VCH Verlag; European Journal of Organic Chemistry; 10-2024; 1-18
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/247287
identifier_str_mv Barata Vallejo, Sebastian; Yerien, Damián Emilio; Zottola, Agustín Ariel; Postigo, Jose Alberto; Direct Introduction of Perfluoroacyl (−CORF) Groups into Organic Substrates; Wiley VCH Verlag; European Journal of Organic Chemistry; 10-2024; 1-18
1434-193X
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://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202400898
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.202400898
dc.rights.none.fl_str_mv info:eu-repo/semantics/embargoedAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv embargoedAccess
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 13.22299

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