Photoinduced perfluorobutylation of organic substrates in aqueous media

Abstract

Hydroperfluorobutylation of a series of electron-deficient and electron-rich alkenes through consecutive radical reactions employing perfluorobutyl iodide, n-C4F9I, and (Me3Si)3SiH as chain carrier/hydrogen atom donor is described. The photoinduced Halogen Atom Transfer (HAT) reactions of both olefins and alkynes with n-C4F9I are also shown to be achieved efficiently in aqueous mixtures. On the other hand, aromatic and heteroaromatic substrates can be perfluorobutylated with high efficiency in a photoinduced fashion by means of a Homolytic Aromatic Substitution (SHA) process which involves an Electron Transfer (ET) and a Proton Transfer (PT) step.