Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media

Autores
Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; Bonesi, Sergio Mauricio; Argüello, Juan Elias; Postigo, Jose Alberto
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Perfluorobutylation of a series of benzo- and dibenzo-(hetero)aromatic compounds without formal leaving groups is achieved efficiently in organic solvent: water mixtures under photostimulation. The methodology is compared to previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The global reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence affords the products. This constitutes the first report for a direct perfluoroalkylation strategy of dibenzo(hetero)arenes without formal leaving groups.
Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica Ii; Argentina
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Quimica Organica. Catedra de Quimica Organica I; Argentina
Fil: Torviso, Maria del Rosario. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica Ii; Argentina
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Argüello, Juan Elias. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Quimica Organica. Catedra de Quimica Organica I; Argentina
Materia
Homolytic Aromatic Substitution
Perfluoroalkylation
Dibenzoheteroarenes
C-H Perfluoroalkylation
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/8271
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous mediaLantaño, BeatrizBarata Vallejo, SebastianTorviso, Maria del RosarioBonesi, Sergio MauricioArgüello, Juan EliasPostigo, Jose AlbertoHomolytic Aromatic SubstitutionPerfluoroalkylationDibenzoheteroarenesC-H Perfluoroalkylationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Perfluorobutylation of a series of benzo- and dibenzo-(hetero)aromatic compounds without formal leaving groups is achieved efficiently in organic solvent: water mixtures under photostimulation. The methodology is compared to previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The global reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence affords the products. This constitutes the first report for a direct perfluoroalkylation strategy of dibenzo(hetero)arenes without formal leaving groups.Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica Ii; ArgentinaFil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Quimica Organica. Catedra de Quimica Organica I; ArgentinaFil: Torviso, Maria del Rosario. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica Ii; ArgentinaFil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Argüello, Juan Elias. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Quimica Organica. Catedra de Quimica Organica I; ArgentinaElsevier2014-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/8271Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; Bonesi, Sergio Mauricio; Argüello, Juan Elias; et al.; Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media; Elsevier; Journal Of Fluorine Chemistry; 161; 3-2014; 149-1550022-1139enginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jfluchem.2014.02.008info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S002211391400061Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:43Zoai:ri.conicet.gov.ar:11336/8271instacron: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 09:39:43.627CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
title Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
spellingShingle Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
Lantaño, Beatriz
Homolytic Aromatic Substitution
Perfluoroalkylation
Dibenzoheteroarenes
C-H Perfluoroalkylation
title_short Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
title_full Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
title_fullStr Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
title_full_unstemmed Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
title_sort Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media
dc.creator.none.fl_str_mv Lantaño, Beatriz
Barata Vallejo, Sebastian
Torviso, Maria del Rosario
Bonesi, Sergio Mauricio
Argüello, Juan Elias
Postigo, Jose Alberto
author Lantaño, Beatriz
author_facet Lantaño, Beatriz
Barata Vallejo, Sebastian
Torviso, Maria del Rosario
Bonesi, Sergio Mauricio
Argüello, Juan Elias
Postigo, Jose Alberto
author_role author
author2 Barata Vallejo, Sebastian
Torviso, Maria del Rosario
Bonesi, Sergio Mauricio
Argüello, Juan Elias
Postigo, Jose Alberto
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Homolytic Aromatic Substitution
Perfluoroalkylation
Dibenzoheteroarenes
C-H Perfluoroalkylation
topic Homolytic Aromatic Substitution
Perfluoroalkylation
Dibenzoheteroarenes
C-H Perfluoroalkylation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Perfluorobutylation of a series of benzo- and dibenzo-(hetero)aromatic compounds without formal leaving groups is achieved efficiently in organic solvent: water mixtures under photostimulation. The methodology is compared to previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The global reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence affords the products. This constitutes the first report for a direct perfluoroalkylation strategy of dibenzo(hetero)arenes without formal leaving groups.
Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica Ii; Argentina
Fil: Barata Vallejo, Sebastian. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Quimica Organica. Catedra de Quimica Organica I; Argentina
Fil: Torviso, Maria del Rosario. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica. Química Orgánica Ii; Argentina
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Argüello, Juan Elias. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Postigo, Jose Alberto. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Quimica Organica. Catedra de Quimica Organica I; Argentina
description Perfluorobutylation of a series of benzo- and dibenzo-(hetero)aromatic compounds without formal leaving groups is achieved efficiently in organic solvent: water mixtures under photostimulation. The methodology is compared to previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The global reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence affords the products. This constitutes the first report for a direct perfluoroalkylation strategy of dibenzo(hetero)arenes without formal leaving groups.
publishDate 2014
dc.date.none.fl_str_mv 2014-03
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/11336/8271
Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; Bonesi, Sergio Mauricio; Argüello, Juan Elias; et al.; Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media; Elsevier; Journal Of Fluorine Chemistry; 161; 3-2014; 149-155
0022-1139
url http://hdl.handle.net/11336/8271
identifier_str_mv Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; Bonesi, Sergio Mauricio; Argüello, Juan Elias; et al.; Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media; Elsevier; Journal Of Fluorine Chemistry; 161; 3-2014; 149-155
0022-1139
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jfluchem.2014.02.008
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S002211391400061X
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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