The electron-deficient iron(III) complex of 5,10,15- tris(pentafluorophenyl)corrole catalyzes the efficient oxidation of hydrocarbons using PhI(OAc)2 as an mild oxygen source. Excellent selectivity and high catalytic efficiency (with up to 1400 TON) have been achieved for alkene epoxidation. Competitive catalytic oxidation of ethylbenzene and ethlybenzene-d10 revealed a kinetic isotope effect (KIE) of kH/kD = 3.6±0.2 at 298 K, similar to the KIE reported for an electron-deficient iron(V)-oxo corrole species. A linear Hammett correlation (ρ+ = -0.79, R = 0.996) was obtained. This promising oxygen transfer process is mechanistically rationalized in terms of a putative high-valent iron(V)-oxo species as the active oxidant.

Highly efficient and selective epoxidation catalyzed by iron corrole complexes and iodobenzene diacetate

249th National Meeting (2015)

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