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

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 Haloge...

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Autor principal: Vázquez, Alvaro Joaquín
Publicado: 2012
Materias:
Halogen atom transfer
Perfluoroalkyl-substituted compounds
Radical perfluoroalkylation in water
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00221139_v135_n_p137_Slodowicz
http://hdl.handle.net/20.500.12110/paper_00221139_v135_n_p137_Slodowicz
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling paper:paper_00221139_v135_n_p137_Slodowicz2023-06-08T14:45:57Z Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water Vázquez, Alvaro Joaquín Halogen atom transfer Perfluoroalkyl-substituted compounds Radical perfluoroalkylation in water 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. © 2011 Elsevier B.V. All rights reserved. Fil:Vázquez, A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2012 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00221139_v135_n_p137_Slodowicz http://hdl.handle.net/20.500.12110/paper_00221139_v135_n_p137_Slodowicz
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Halogen atom transfer
Perfluoroalkyl-substituted compounds
Radical perfluoroalkylation in water
spellingShingle Halogen atom transfer
Perfluoroalkyl-substituted compounds
Radical perfluoroalkylation in water
Vázquez, Alvaro Joaquín
Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water
topic_facet Halogen atom transfer
Perfluoroalkyl-substituted compounds
Radical perfluoroalkylation in water
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. © 2011 Elsevier B.V. All rights reserved.
author Vázquez, Alvaro Joaquín
author_facet Vázquez, Alvaro Joaquín
author_sort Vázquez, Alvaro Joaquín
title Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds 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
publishDate 2012
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00221139_v135_n_p137_Slodowicz
http://hdl.handle.net/20.500.12110/paper_00221139_v135_n_p137_Slodowicz
work_keys_str_mv AT vazquezalvarojoaquin lightinducediodoperfluoroalkylationreactionsofcarboncarbonmultiplebondsinwater
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