Substituent modulation of mild fluorination of aromatic molecules with caesium fluoroxysulphate

Article abstract of DOI:10.1016/S0022-1139(00)80337-1

Functionalization of mono- and di-substituted benzene derivative with CsSO4F has been modulated by substituents on the benzene ring. α-Hydroxyalkylbenzenes, with a deactivated ring, were oxidized to phenones, while fluorodealkylation was achieved in high yield when electron-donating groups were present in a para position. Electron-withdrawing substituents favoured chain fluorofunctionalization in alkylbenzenes, while ring fluorination was found exclusively in acylamino-derivatized alkylbenzenes; fluoro-addition products were formed in the case of p-alkoxy-substituted alkylbenzene derivatives.