Synthesis of the hemin of β-tetrakis(trifluoromethyl)- meso-tetraphenylporphyrin and its evaluation as a P-450 mimic

Abstract

The hemin of β-tetrakis(trifluoromethyl)- meso-tetraphenylporphyrin has been synthesized. Conventional methods for iron insertion failed; iron in low oxidation states (0 or II) brought about reduction of the macrocycle and Fe(III) failed to insert. Thus, insertion of iron into the macrocycle required the formation of the lithium complex, from lithium bis(trimethylsilyl)amide, followed by ferrous chloride. The novel hemin was tested as a catalyst for oxidations of cyclohexane and cyclohexene using iodosylbenzene as an oxidant and was found to be ineffective.