Perfluorobutylation of benzo(hetero)arenes in aqueous media

Perfluorobutylation of a series of benzo(hetero)aromatic compounds without formal leaving groups is achieved efficaciously in organic solvent-water mixtures under photostimulation. The methodology is compared with previously reported trifluoromethylation strategies of these nuclei in terms of produc...

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Detalles Bibliográficos
Autores: Lantaño, Beatriz, Barata Vallejo, Sebastian, Torviso, Maria del Rosario, García, Selva M., Tinnirello, Aldana, Postigo, Jose Alberto
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2014
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/30544
Acceso en línea:http://hdl.handle.net/11336/30544
Access Level:acceso abierto
Palabra clave:Radical reactions in aqueous media
C-H perfluoroalkylation
Homolytic aromatic substitution
Perfluoroalkylation
Dibenzoheteroarenes
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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spelling Perfluorobutylation of benzo(hetero)arenes in aqueous mediaLantaño, BeatrizBarata Vallejo, SebastianTorviso, Maria del RosarioGarcía, Selva M.Tinnirello, AldanaPostigo, Jose AlbertoRadical reactions in aqueous mediaC-H perfluoroalkylationHomolytic aromatic substitutionPerfluoroalkylationDibenzoheteroareneshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Perfluorobutylation of a series of benzo(hetero)aromatic compounds without formal leaving groups is achieved efficaciously in organic solvent-water mixtures under photostimulation. The methodology is compared with previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence leads to the products.Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: 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: Torviso, Maria del Rosario. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: García, Selva M.. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Tinnirello, Aldana. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; 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; ArgentinaBiointerface Research2014-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/30544Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; García, Selva M.; Tinnirello, Aldana; et al.; Perfluorobutylation of benzo(hetero)arenes in aqueous media; Biointerface Research; Biointerface Research in Applied Chemistry; 4; 5; 10-2014; 861-8642069-5837CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://biointerfaceresearch.com/?page_id=829info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:15:59Zoai:ri.conicet.gov.ar:11336/30544instacron: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:34982024-05-08 14:16:00.152CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Perfluorobutylation of benzo(hetero)arenes in aqueous media
title Perfluorobutylation of benzo(hetero)arenes in aqueous media
spellingShingle Perfluorobutylation of benzo(hetero)arenes in aqueous media
Lantaño, Beatriz
Radical reactions in aqueous media
C-H perfluoroalkylation
Homolytic aromatic substitution
Perfluoroalkylation
Dibenzoheteroarenes
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Perfluorobutylation of benzo(hetero)arenes in aqueous media
title_full Perfluorobutylation of benzo(hetero)arenes in aqueous media
title_fullStr Perfluorobutylation of benzo(hetero)arenes in aqueous media
title_full_unstemmed Perfluorobutylation of benzo(hetero)arenes in aqueous media
title_sort Perfluorobutylation of benzo(hetero)arenes in aqueous media
dc.creator.none.fl_str_mv Lantaño, Beatriz
Barata Vallejo, Sebastian
Torviso, Maria del Rosario
García, Selva M.
Tinnirello, Aldana
Postigo, Jose Alberto
author Lantaño, Beatriz
author_facet Lantaño, Beatriz
Barata Vallejo, Sebastian
Torviso, Maria del Rosario
García, Selva M.
Tinnirello, Aldana
Postigo, Jose Alberto
author_role author
author2 Barata Vallejo, Sebastian
Torviso, Maria del Rosario
García, Selva M.
Tinnirello, Aldana
Postigo, Jose Alberto
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Radical reactions in aqueous media
C-H perfluoroalkylation
Homolytic aromatic substitution
Perfluoroalkylation
Dibenzoheteroarenes
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Radical reactions in aqueous media
C-H perfluoroalkylation
Homolytic aromatic substitution
Perfluoroalkylation
Dibenzoheteroarenes
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description Perfluorobutylation of a series of benzo(hetero)aromatic compounds without formal leaving groups is achieved efficaciously in organic solvent-water mixtures under photostimulation. The methodology is compared with previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence leads to the products.
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/11336/30544
Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; García, Selva M.; Tinnirello, Aldana; et al.; Perfluorobutylation of benzo(hetero)arenes in aqueous media; Biointerface Research; Biointerface Research in Applied Chemistry; 4; 5; 10-2014; 861-864
2069-5837
CONICET Digital
CONICET
url http://hdl.handle.net/11336/30544
identifier_str_mv Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; García, Selva M.; Tinnirello, Aldana; et al.; Perfluorobutylation of benzo(hetero)arenes in aqueous media; Biointerface Research; Biointerface Research in Applied Chemistry; 4; 5; 10-2014; 861-864
2069-5837
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://biointerfaceresearch.com/?page_id=829
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Biointerface Research
publisher.none.fl_str_mv Biointerface Research
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15,811543

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