Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water

Autores
Slodowicz, Mariel Pamela; Barata Vallejo, Sebastian; Vázquez, A.; Sbarbati Nudelman, N.; Postigo, Jose Alberto
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work we have undertaken the radical-induced addition of 1-iodo-n-perfluorobutane onto electron-rich alkenes, alkenes with electron withdrawing groups, and alkynes in water, initiated photochemically. The lack of hydrogen donor (i.e.: (Me 3Si) 3SiH) in our reaction medium facilitates a Halogen Atom-transfer reaction (HAT), affording the respective perfluorobutylated alkyl and alkenyl halides (iodides) in good yields in water. We have also found that water exerts a relevant solvent effect on the rates of perfluoroalkyl radical additions onto double and triple bonds. The stereoselectivity of the radical addition reaction of alkynes is studied. The novelty of this work relies on the photochemical generation of fluorinated radicals in water, and the Halogen Atom-transfer addition reactions of iodoperfluoroalkanes onto carbon-carbon unsaturated bonds in water induced by light.
Fil: Slodowicz, Mariel Pamela. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Vázquez, A.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Sbarbati Nudelman, N.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
HALOGEN ATOM TRANSFER
PERFLUOROALKYL-SUBSTITUTED COMPOUNDS
RADICAL PERFLUOROALKYLATION IN WATER
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:11336/189029
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/189029
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in waterSlodowicz, Mariel PamelaBarata Vallejo, SebastianVázquez, A.Sbarbati Nudelman, N.Postigo, Jose AlbertoHALOGEN ATOM TRANSFERPERFLUOROALKYL-SUBSTITUTED COMPOUNDSRADICAL PERFLUOROALKYLATION IN WATERhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In this work we have undertaken the radical-induced addition of 1-iodo-n-perfluorobutane onto electron-rich alkenes, alkenes with electron withdrawing groups, and alkynes in water, initiated photochemically. The lack of hydrogen donor (i.e.: (Me 3Si) 3SiH) in our reaction medium facilitates a Halogen Atom-transfer reaction (HAT), affording the respective perfluorobutylated alkyl and alkenyl halides (iodides) in good yields in water. We have also found that water exerts a relevant solvent effect on the rates of perfluoroalkyl radical additions onto double and triple bonds. The stereoselectivity of the radical addition reaction of alkynes is studied. The novelty of this work relies on the photochemical generation of fluorinated radicals in water, and the Halogen Atom-transfer addition reactions of iodoperfluoroalkanes onto carbon-carbon unsaturated bonds in water induced by light.Fil: Slodowicz, Mariel Pamela. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Vázquez, A.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Sbarbati Nudelman, N.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaElsevier Science SA2012-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/189029Slodowicz, Mariel Pamela; Barata Vallejo, Sebastian; Vázquez, A.; Sbarbati Nudelman, N.; Postigo, Jose Alberto; Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water; Elsevier Science SA; Journal of Fluorine Chemistry; 135; 3-2012; 137-1430022-1139CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jfluchem.2011.10.002info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:46:13Zoai:ri.conicet.gov.ar:11336/189029instacron: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 10:46:13.294CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
title Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
spellingShingle Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
Slodowicz, Mariel Pamela
HALOGEN ATOM TRANSFER
PERFLUOROALKYL-SUBSTITUTED COMPOUNDS
RADICAL PERFLUOROALKYLATION IN WATER
title_short Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
title_full Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
title_fullStr Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
title_full_unstemmed Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
title_sort Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
dc.creator.none.fl_str_mv Slodowicz, Mariel Pamela
Barata Vallejo, Sebastian
Vázquez, A.
Sbarbati Nudelman, N.
Postigo, Jose Alberto
author Slodowicz, Mariel Pamela
author_facet Slodowicz, Mariel Pamela
Barata Vallejo, Sebastian
Vázquez, A.
Sbarbati Nudelman, N.
Postigo, Jose Alberto
author_role author
author2 Barata Vallejo, Sebastian
Vázquez, A.
Sbarbati Nudelman, N.
Postigo, Jose Alberto
author2_role author
author
author
author
dc.subject.none.fl_str_mv HALOGEN ATOM TRANSFER
PERFLUOROALKYL-SUBSTITUTED COMPOUNDS
RADICAL PERFLUOROALKYLATION IN WATER
topic HALOGEN ATOM TRANSFER
PERFLUOROALKYL-SUBSTITUTED COMPOUNDS
RADICAL PERFLUOROALKYLATION IN WATER
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In this work we have undertaken the radical-induced addition of 1-iodo-n-perfluorobutane onto electron-rich alkenes, alkenes with electron withdrawing groups, and alkynes in water, initiated photochemically. The lack of hydrogen donor (i.e.: (Me 3Si) 3SiH) in our reaction medium facilitates a Halogen Atom-transfer reaction (HAT), affording the respective perfluorobutylated alkyl and alkenyl halides (iodides) in good yields in water. We have also found that water exerts a relevant solvent effect on the rates of perfluoroalkyl radical additions onto double and triple bonds. The stereoselectivity of the radical addition reaction of alkynes is studied. The novelty of this work relies on the photochemical generation of fluorinated radicals in water, and the Halogen Atom-transfer addition reactions of iodoperfluoroalkanes onto carbon-carbon unsaturated bonds in water induced by light.
Fil: Slodowicz, Mariel Pamela. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Vázquez, A.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Sbarbati Nudelman, N.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Postigo, Jose Alberto. Universidad de Belgrano; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description In this work we have undertaken the radical-induced addition of 1-iodo-n-perfluorobutane onto electron-rich alkenes, alkenes with electron withdrawing groups, and alkynes in water, initiated photochemically. The lack of hydrogen donor (i.e.: (Me 3Si) 3SiH) in our reaction medium facilitates a Halogen Atom-transfer reaction (HAT), affording the respective perfluorobutylated alkyl and alkenyl halides (iodides) in good yields in water. We have also found that water exerts a relevant solvent effect on the rates of perfluoroalkyl radical additions onto double and triple bonds. The stereoselectivity of the radical addition reaction of alkynes is studied. The novelty of this work relies on the photochemical generation of fluorinated radicals in water, and the Halogen Atom-transfer addition reactions of iodoperfluoroalkanes onto carbon-carbon unsaturated bonds in water induced by light.
publishDate 2012
dc.date.none.fl_str_mv 2012-03
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/11336/189029
Slodowicz, Mariel Pamela; Barata Vallejo, Sebastian; Vázquez, A.; Sbarbati Nudelman, N.; Postigo, Jose Alberto; Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water; Elsevier Science SA; Journal of Fluorine Chemistry; 135; 3-2012; 137-143
0022-1139
CONICET Digital
CONICET
url http://hdl.handle.net/11336/189029
identifier_str_mv Slodowicz, Mariel Pamela; Barata Vallejo, Sebastian; Vázquez, A.; Sbarbati Nudelman, N.; Postigo, Jose Alberto; Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water; Elsevier Science SA; Journal of Fluorine Chemistry; 135; 3-2012; 137-143
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.2011.10.002
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
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_ 1844614503196524544
score 13.070432

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