Iron polynitroporphyrins bearing up to eight β-nitro groups as interesting new catalysts for H2O2-dependent hydrocarbonoxidation: unusual regioselectivity in hydroxylation of alkoxybenzenes

Abstract

A series of iron porphyrins bearing one to eight β-nitro substituents were synthesized and evaluated as catalysts for hydrocarbon oxidation with H₂O₂; iron porphyrins bearing five or six β-nitro groups were the best catalysts for cyclooctene epoxidation and adamantane or anisole hydroxylation without need of a cocatalyst, and led to very different regioselectivities with either H₂O₂ or PhIO as oxidants, as shown by an unusual ortho-hydroxylation of alkoxybenzenes highly favored in the H₂O₂-dependent oxidations.