Mechanism of Arene Hydroxylation by Vanadium Picolinato Peroxo Complexes

Article abstract of DOI:10.1021/jo00100a029

The mechanism of the reaction of VO(O2)PIC(H2O)2 (PIC = picolinic acid anion) with benzene and substituted benzenes in CH3CN, affording the corresponding phenols together with dioxygen, has been further investigated.The reaction is a radical chain process whose initiation produces the actual oxidant which may be described as a radical anion derived from the peroxovanadium complex, possessing, however, a marked electrophilic character.In the propagation steps such species react either with the original peroxo complex yielding dioxygen or with the aromatic substrates affording phenols via the formation of an intermediate.