Direct CH perfluoroalkylation of (di)benzo(hetero)arenes in aqueous media
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 term...
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| Autores principales: | , , , , , |
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| Formato: | JOUR |
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00221139_v161_n_p149_Lantano |
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| Sumario: | 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. |
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