Visible-Light-Mediated Radical Arylations Using a Fluorescein-Derived Diazonium Salt: Reactions Proceeding via an Intramolecular Forth and Back Electron Transfer.

Functionalizations of arenes and alkenes via additive-free radical reactions using highly photosensitive, fluorescein-derived diazonium salts are described. The particular properties of the diazonium salts enable unique Meerwein-type carbohydroxylations of non-activated alkenes, which can be rationalized by a reaction mechanism involving forth and back electron transfer from and to the xanthene subunit of the fluorescein moiety.