Hydroperoxidation of methane and other alkanes with H 2O 2 catalyzed by a dinuclear iron complex and an amino acid

Abstract

The compound [Fe 2(HPTB)(μ-OH)(NO 3) 2](NO 3) 2·CH 3OH·2H 2O ( 1 ) containing a dinuclear iron(III) complex in which HPTB= N, N, N′, N′-tetrakis(2-benzimidazolylmethyl)-2-hydroxo-1,3-diaminopropane catalyzes the oxidation of alkanes with hydrogen peroxide in acetonitrile solution at room temperature only if certain amino acids (pyrazine-2-carboxylic, pyrazine-2,3-dicarboxylic or picolinic acid) are added to the reaction mixture. Alkyl hydroperoxides are formed as main reaction products. The turnover numbers attain 140 for cyclohexane, 21 for ethane and four for methane oxidation. The oxidation proceeds non-stereoselectively and bond selectivity parameters are low which testifies the participation of hydroxyl radicals in alkane functionalization.