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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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00221139_v135_n_p137_Slodowicz |
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todo:paper_00221139_v135_n_p137_Slodowicz2023-10-03T14:26:35Z Light-induced iodoperfluoroalkylation reactions of carbon-carbon multiple bonds in water Slodowicz, M. Barata-Vallejo, S. Vázquez, A. Nudelman, N.S. Postigo, A. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 Slodowicz, M. Barata-Vallejo, S. Vázquez, A. Nudelman, N.S. Postigo, A. 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. |
| format |
JOUR |
| author |
Slodowicz, M. Barata-Vallejo, S. Vázquez, A. Nudelman, N.S. Postigo, A. |
| author_facet |
Slodowicz, M. Barata-Vallejo, S. Vázquez, A. Nudelman, N.S. Postigo, A. |
| author_sort |
Slodowicz, M. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00221139_v135_n_p137_Slodowicz |
| work_keys_str_mv |
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1807323699687194624 |