Direct C-H perfluoroalkylaion of (di)benzo(hetero)arenes in aqueous media

LANTAÑO BEATRIZ; BARAJA VALLEJO SEBASTIAN; TORVISIO M. ROSARIO; BONESI S. M.; ARGUELLO JUAN; POSTIGO J. ALBERTO

JOURNAL OF FLUORINE CHEMISTRY

ELSEVIER SCIENCE SA

Lugar: Amsterdam; Año: 2014 vol. 161 p. 149 - 155

0022-1139

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.