dc.creatorBarata-Vallejo, Sebastián
dc.creatorPostigo, Al
dc.date.accessioned2014-07-25T18:18:04Z
dc.date.accessioned2022-11-09T15:00:30Z
dc.date.available2014-07-25T18:18:04Z
dc.date.available2022-11-09T15:00:30Z
dc.date.created2014-07-25T18:18:04Z
dc.date.issued2010
dc.identifierhttp://repositorio.ub.edu.ar/handle/123456789/2720
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/5167951
dc.description.abstractPerfluoroalkyl-substituted compounds are regarded as important components of fluorophors and for the introduction of fluorous tags into organic substrates. Their syntheses in organic solvents are achieved through different methods, among which, the addition of perfluoroalkyl radicals to unsaturated bonds represents a convenient choice. On the other hand, intermolecular radical reactions in water have attracted the attention of synthetic chemists as a strategic route to carbon−carbon bond formation reactions. In this paper we undertook the intermolecular addition of perfluoroalkyl radicals on electron rich alkenes and alkenes with electron withdrawing groups in water, mediated by silyl radicals, and obtained perfluoroalkyl-substituted compounds in fairly good yields. The radical triggering events employed consist of the thermal decomposition of an azo compound and the dioxygen initiation. Our results indicate that for intermolecular carbon−carbon bond formation reactions mediated by (Me3Si)3SiH, the decomposition of the azo compound 1,1′-azobis(cyclohexanecarbonitrile) (ACCN) is the best radical initiator. We also found that water exerts a relevant solvent effect on the rates of perfluoroalkyl radical additions onto double bonds and the H atom abstraction from the silane. Our account provides a versatile and convenient method to achieve perfluoroalkylation reactions of alkenes in water to render perfluoroalkylated alkanes as key intermediates in the synthesis of fluorophors and other fluorinated materials. This is the first report where perfluoroalkyl-substituted alkanes are synthesized through intermolecular radical carbon−carbon bond formation reactions in water, mediated by silyl radicals.
dc.languageen
dc.publisherUniversidad de Belgrano - Facultad de Ciencias Exactas y Naturales - Proyectos de Investigación
dc.relationThe Journal of Organic Chemistry (JOC);2010, 75 (18), pp 6141–6148
dc.subjectReactions of Olefins in Water
dc.subjectMediated Intermolecular
dc.subjectmediada intermolecular
dc.subjectReacciones de olefinas en Agua
dc.title(Me3Si)3SiH-Mediated Intermolecular Radical Perfluoroalkylation Reactions of Olefins in Water
dc.typeArtículos de revistas


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