Direct C?H Perfluoroalkylation of (Di)benzo(hetero)arenes in Aqueous Media

BEATRIZ LANTAÑO; BARATA VALLEJO, S; TORVISO, M.R.; BONESI, SERGIO M.; ARGUELLO, J.E.; A POSTIGO

JOURNAL OF FLUORINE CHEMISTRY

ELSEVIER SCIENCE SA

Lugar: Amsterdam-http://dx.doi.org/10.1016/j.jfluchem.2014.02.008; Año: 2014 vol. 161 p. 149 - 155

0022-1139

http://dx.doi.org/10.1016/j.jfluchem.2014.02.008 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.