Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts

Autores
Torviso, Maria del Rosario; Mansilla, Daniela Soledad; Garcia, Selva; Lantaño, Beatriz; Barata Vallejo, Sebastian; Postigo, Jose Alberto
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Novel and high-yielding protocols for the late-stage synthesis of 3-perfluoroalkyl-substituted coumarin derivatives employing either perfluoroalkyl iodides RFI or sodium perfluoroalkylsulfinate salts NaSO2RF as perfluoroalkyl RF radical precursors is presented. The electron-catalyzed methodologies make use of two comparative and parallel protocols as an entry to the production of RF radicals: (i) from NaSO2Rf sources and the thermal tert-butylhydroperoxide (TBHP) radical initiation in MeCN: CH2Cl2 as organic solvent mixture, and (ii) from commercial RFI and the photoorganocatalyst anthraquinone-2-sulfonic acid as the room-light initiation process in DMF: CH2Cl2 as mixture of solvents.
Fil: Torviso, Maria del Rosario. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Mansilla, Daniela Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Garcia, Selva. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Materia
Perfluoroalkylation
Coumarin
Electron-Catalyzed
Photocatalysis
3-Perfluoroalkylated Coumarin
Potassium Oxalate
Nivel de accesibilidad
acceso abierto
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:11336/47840
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/47840
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate saltsTorviso, Maria del RosarioMansilla, Daniela SoledadGarcia, SelvaLantaño, BeatrizBarata Vallejo, SebastianPostigo, Jose AlbertoPerfluoroalkylationCoumarinElectron-CatalyzedPhotocatalysis3-Perfluoroalkylated CoumarinPotassium Oxalatehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Novel and high-yielding protocols for the late-stage synthesis of 3-perfluoroalkyl-substituted coumarin derivatives employing either perfluoroalkyl iodides RFI or sodium perfluoroalkylsulfinate salts NaSO2RF as perfluoroalkyl RF radical precursors is presented. The electron-catalyzed methodologies make use of two comparative and parallel protocols as an entry to the production of RF radicals: (i) from NaSO2Rf sources and the thermal tert-butylhydroperoxide (TBHP) radical initiation in MeCN: CH2Cl2 as organic solvent mixture, and (ii) from commercial RFI and the photoorganocatalyst anthraquinone-2-sulfonic acid as the room-light initiation process in DMF: CH2Cl2 as mixture of solvents.Fil: Torviso, Maria del Rosario. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Mansilla, Daniela Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Garcia, Selva. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaElsevier Science Sa2017-05info: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/11336/47840Torviso, Maria del Rosario; Mansilla, Daniela Soledad; Garcia, Selva; Lantaño, Beatriz; Barata Vallejo, Sebastian; et al.; Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts; Elsevier Science Sa; Journal of Fluorine Chemistry; 197; 5-2017; 42-480022-1139CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jfluchem.2017.03.005info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022113917300490info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T09:38:44Zoai:ri.conicet.gov.ar:11336/47840instacron: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:34982025-11-12 09:38:45.192CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
title Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
spellingShingle Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
Torviso, Maria del Rosario
Perfluoroalkylation
Coumarin
Electron-Catalyzed
Photocatalysis
3-Perfluoroalkylated Coumarin
Potassium Oxalate
title_short Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
title_full Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
title_fullStr Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
title_full_unstemmed Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
title_sort Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts
dc.creator.none.fl_str_mv Torviso, Maria del Rosario
Mansilla, Daniela Soledad
Garcia, Selva
Lantaño, Beatriz
Barata Vallejo, Sebastian
Postigo, Jose Alberto
author Torviso, Maria del Rosario
author_facet Torviso, Maria del Rosario
Mansilla, Daniela Soledad
Garcia, Selva
Lantaño, Beatriz
Barata Vallejo, Sebastian
Postigo, Jose Alberto
author_role author
author2 Mansilla, Daniela Soledad
Garcia, Selva
Lantaño, Beatriz
Barata Vallejo, Sebastian
Postigo, Jose Alberto
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Perfluoroalkylation
Coumarin
Electron-Catalyzed
Photocatalysis
3-Perfluoroalkylated Coumarin
Potassium Oxalate
topic Perfluoroalkylation
Coumarin
Electron-Catalyzed
Photocatalysis
3-Perfluoroalkylated Coumarin
Potassium Oxalate
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Novel and high-yielding protocols for the late-stage synthesis of 3-perfluoroalkyl-substituted coumarin derivatives employing either perfluoroalkyl iodides RFI or sodium perfluoroalkylsulfinate salts NaSO2RF as perfluoroalkyl RF radical precursors is presented. The electron-catalyzed methodologies make use of two comparative and parallel protocols as an entry to the production of RF radicals: (i) from NaSO2Rf sources and the thermal tert-butylhydroperoxide (TBHP) radical initiation in MeCN: CH2Cl2 as organic solvent mixture, and (ii) from commercial RFI and the photoorganocatalyst anthraquinone-2-sulfonic acid as the room-light initiation process in DMF: CH2Cl2 as mixture of solvents.
Fil: Torviso, Maria del Rosario. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Mansilla, Daniela Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Garcia, Selva. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Lantaño, Beatriz. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
Fil: Postigo, Jose Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
description Novel and high-yielding protocols for the late-stage synthesis of 3-perfluoroalkyl-substituted coumarin derivatives employing either perfluoroalkyl iodides RFI or sodium perfluoroalkylsulfinate salts NaSO2RF as perfluoroalkyl RF radical precursors is presented. The electron-catalyzed methodologies make use of two comparative and parallel protocols as an entry to the production of RF radicals: (i) from NaSO2Rf sources and the thermal tert-butylhydroperoxide (TBHP) radical initiation in MeCN: CH2Cl2 as organic solvent mixture, and (ii) from commercial RFI and the photoorganocatalyst anthraquinone-2-sulfonic acid as the room-light initiation process in DMF: CH2Cl2 as mixture of solvents.
publishDate 2017
dc.date.none.fl_str_mv 2017-05
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/11336/47840
Torviso, Maria del Rosario; Mansilla, Daniela Soledad; Garcia, Selva; Lantaño, Beatriz; Barata Vallejo, Sebastian; et al.; Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts; Elsevier Science Sa; Journal of Fluorine Chemistry; 197; 5-2017; 42-48
0022-1139
CONICET Digital
CONICET
url http://hdl.handle.net/11336/47840
identifier_str_mv Torviso, Maria del Rosario; Mansilla, Daniela Soledad; Garcia, Selva; Lantaño, Beatriz; Barata Vallejo, Sebastian; et al.; Late-stage electron-catalyzed perfluoroalkylation of coumarin derivatives—Thermal fluoroalkyl radical production from sodium perfluoroalkyl sulfinate salts; Elsevier Science Sa; Journal of Fluorine Chemistry; 197; 5-2017; 42-48
0022-1139
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jfluchem.2017.03.005
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022113917300490
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 Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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_ 1848597398260023296
score 13.24909

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