Selective hydroxylation of alkanes catalyzed by iron(IV)corrole

The complex meso-tris(pentafluorophenyl)corrolatoiron(IV)chloride [(F15TPC)FeCl] emerged as efficient catalyst in hydroxylating alkanes at room temperature. Cyclohexane and adamantane have been oxidized to the corresponding alcohols using m-chloroperbenzoic acid (m-CPBA) as terminal oxidant. Cyclohexane has been converted to cyclohexanol in 50% yield with 100% selectivity. Adamantane has also been hydroxylated up to 75% overall yield under identical reaction condition. Significantly high regioselectivity in adamantane oxidation has been observed. The reactive intermediates have been quantitatively trapped by 2,4,6-tri-t-butylphenol (TTBP). Kinetic analysis of the (F15TPC)FeCl-catalyzed oxidation of TTBP has found consistent with rapid reaction of organic substrate with an intermediate formed in the first and rate-determining step. (C) 2010 Elsevier B.V. All rights reserved.