Fe2+-catalyzed heterolytic RO-OH bond cleavage and substrate oxidation: a functional synthetic non-heme iron monooxygenase system.
The reaction of [Fe22+(H2Hbamb)2(N-MeIm)2], [1], a binuclear, non-heme iron complex, with 2-methyl-1-phenylprop-2-yl hydroperoxide (MPPH) shows that [1] induces heterolytic cleavage of the peroxy O-O bond. Catalytic atom transfer reactions (1:MPPH:PhSMe 1:596:6011) resulted in the highly efficient (99 +/- 1%), catalytic oxidation of phenyl methyl sulfide to phenyl methyl sulfoxide/sulfone (T.N. = 500/11 respectively) and cyclohexane to cyclohexanol/cyclohexanone (T.N. = 230/5 respectively) showing the highly efficient, catalytic capacity of [1] to carry out oxygen insertion chemistry.
Foster
Trina L
TL
Department of Chemistry, Boston University, Massachusetts 02215, USA.
Caradonna
John P
JP
D040761:Biomimetic Materials / Q000737:chemistry*; D003510:Cyclohexanes / Q000737:chemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010105:Oxygenases / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry
C474099:2-methyl-1-phenylprop-2-yl hydroperoxide; D003510:Cyclohexanes; D005296:Ferrous Compounds; D010545:Peroxides; D013440:Sulfides; C093850:methylphenylsulfide; D010105:Oxygenases