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
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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
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Palabras clave: | CH perfluoroalkylation; Dibenzoheteroarenes; Homolytic aromatic substitution; Perfluoroalkylation; Radical reactions aqueous in media |
Año: | 2014
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Volumen: | 161
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Página de inicio: | 149
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Página de fin: | 155
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DOI: |
http://dx.doi.org/10.1016/j.jfluchem.2014.02.008 |
Título revista: | Journal of Fluorine Chemistry
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Título revista abreviado: | J. Fluor. Chem.
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ISSN: | 00221139
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CODEN: | JFLCA
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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