The oxidation of olefins with O2 and NaBH4 catalyzed by manganese meso-tetrakis(p-sulfonatophenyl)porphin

The oxidations of olefins with molecular oxygen and a reducing agent couple catalyzed by metal meso-tetrakis(p-sulfonatophenyl)porphins [Me(TPPS)] in methanol solvent was studied and compared with that by metal meso-tetraphenylporphin [Me(TPP)]. In the oxidation of cyclohexene by Me(TPPS), Mn(TPPS) coupled with NaBH4 was the most effective for producing cyclohexanol as a main product, and its activity was higher than that of Mn(TPP)Cl. On comparing its activity with that of the Mn(TPPS)/iodosobenzene system capable of producing a high-valent metal oxo-type active species, it was deduced that the Mn(TPPS)/O2/NaBH4 system catalyzed the olefin oxidation by forming a non-metal oxo-type active species.