On the mechanism of catalytic alkene oxidation by molecular oxygen and halogenated iron porphyrins

Add time:07/26/2019    Source:sciencedirect.com

The halogenated porphyrin, 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetrakis(pentafluorophenyl)porphyriato-iron(III) chloride, [Fe(TFPPBr8)Cl], catalyzes the oxidation of cyclohexene in the presence of molecular oxygen or iodosobenzene. With PhIO, 77% epoxide is observed, consistent with a mechanism involving a high-valent metal-oxo species. With dioxygen, however, allylic alcohol and ketone are observed, suggesting a different mechanism. The relatively high activity of the [Fe(TFPPBr8)Cl]O2 system suggests that the reaction involves the formation and decomposition of alkyl peroxides.

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