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Lantaño, B.; Barata-Vallejo, S.; Torviso, M.R.; Bonesi, S.M.; Argüello, J.E.; Postigo, A. "Direct CH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media" (2014) Journal of Fluorine Chemistry. 161:149-155
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Abstract:

Perfluorobutylation of a series of benzo- and dibenzo-(hetero)aromatic compounds without formal leaving groups is achieved efficiently in organic solvent: water mixtures under photostimulation. The methodology is compared to previously reported trifluoromethylation strategies of these nuclei in terms of product yields and regioselectivity. The global reaction is a radical homolytic aromatic substitution process, where the perfluoroalkyl-substituted cyclohexadienyl radical intermediate is first oxidized and then a proton transfer sequence affords the products. This constitutes the first report for a direct perfluoroalkylation strategy of dibenzo(hetero)arenes without formal leaving groups. © 2014 Elsevier B.V.

Registro:

Documento: Artículo
Título:Direct CH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
Autor:Lantaño, B.; Barata-Vallejo, S.; Torviso, M.R.; Bonesi, S.M.; Argüello, J.E.; Postigo, A.
Filiación:Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 954 CP1113, Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, CP 1428, Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Haya de la Torre, esq. Medina Allende, Córdoba, CP5000 Córdoba, Argentina
Palabras clave:CH perfluoroalkylation; Dibenzoheteroarenes; Homolytic aromatic substitution; Perfluoroalkylation; Radical reactions aqueous in media
Año:2014
Volumen:161
Página de inicio:149
Página de fin:155
DOI: http://dx.doi.org/10.1016/j.jfluchem.2014.02.008
Título revista:Journal of Fluorine Chemistry
Título revista abreviado:J. Fluor. Chem.
ISSN:00221139
CODEN:JFLCA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00221139_v161_n_p149_Lantano

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Citas:

---------- APA ----------
Lantaño, B., Barata-Vallejo, S., Torviso, M.R., Bonesi, S.M., Argüello, J.E. & Postigo, A. (2014) . Direct CH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media. Journal of Fluorine Chemistry, 161, 149-155.
http://dx.doi.org/10.1016/j.jfluchem.2014.02.008
---------- CHICAGO ----------
Lantaño, B., Barata-Vallejo, S., Torviso, M.R., Bonesi, S.M., Argüello, J.E., Postigo, A. "Direct CH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media" . Journal of Fluorine Chemistry 161 (2014) : 149-155.
http://dx.doi.org/10.1016/j.jfluchem.2014.02.008
---------- MLA ----------
Lantaño, B., Barata-Vallejo, S., Torviso, M.R., Bonesi, S.M., Argüello, J.E., Postigo, A. "Direct CH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media" . Journal of Fluorine Chemistry, vol. 161, 2014, pp. 149-155.
http://dx.doi.org/10.1016/j.jfluchem.2014.02.008
---------- VANCOUVER ----------
Lantaño, B., Barata-Vallejo, S., Torviso, M.R., Bonesi, S.M., Argüello, J.E., Postigo, A. Direct CH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media. J. Fluor. Chem. 2014;161:149-155.
http://dx.doi.org/10.1016/j.jfluchem.2014.02.008