Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media

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 term...

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Detalles Bibliográficos
Autores: Lantaño, Beatriz, Barata Vallejo, Sebastian, Torviso, Maria del Rosario, Bonesi, Sergio Mauricio, Argüello, Juan Elias, 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:11336/16771
Acceso en línea:http://hdl.handle.net/11336/16771
Access Level:acceso abierto
Palabra clave:Homolytic Aromatic Substitution
Perfluoroalkylation
Dibenzoheteroarenes
C-H Perfluoroalkylation
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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network_acronym_str AR
network_name_str Argentina
repository_id_str
spelling Direct Csingle bondH perfluoroalkylation 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. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; 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: Bonesi, Sergio Mauricio. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Argüello, Juan Elias. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; 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; ArgentinaElsevier Science2014-05info: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/11336/16771Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; Bonesi, Sergio Mauricio; Argüello, Juan Elias; et al.; Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media; Elsevier Science; Journal of Fluorine Chemistry; 161; 5-2014; 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 Técnicas2024-05-08T13:50:41Zoai:ri.conicet.gov.ar:11336/16771instacron: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 13:50:41.545CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
title Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
spellingShingle Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
Lantaño, Beatriz
Homolytic Aromatic Substitution
Perfluoroalkylation
Dibenzoheteroarenes
C-H Perfluoroalkylation
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
title_full Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
title_fullStr Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
title_full_unstemmed Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
title_sort Direct Csingle bondH perfluoroalkylation 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
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic Homolytic Aromatic Substitution
Perfluoroalkylation
Dibenzoheteroarenes
C-H Perfluoroalkylation
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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 2014-05
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/11336/16771
Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; Bonesi, Sergio Mauricio; Argüello, Juan Elias; et al.; Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media; Elsevier Science; Journal of Fluorine Chemistry; 161; 5-2014; 149-155
0022-1139
url http://hdl.handle.net/11336/16771
identifier_str_mv Lantaño, Beatriz; Barata Vallejo, Sebastian; Torviso, Maria del Rosario; Bonesi, Sergio Mauricio; Argüello, Juan Elias; et al.; Direct Csingle bondH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media; Elsevier Science; Journal of Fluorine Chemistry; 161; 5-2014; 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
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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 15,812429

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