Abstract
Iron(III), manganese(III), and cobalt(II) com- plexes of meso-tetrakis(p-chlorophenyl)porphyrin (Fe(TCl- PP)X, Mn(TClPP)X, and Co(TClPP)X, X = Cl or OAc) were immobilized onto 3-aminopropyl-functionalized silica (SF-3-APTS). SF-3-APTS acts as both axial base and support for immobilization of these metalloporphyrins. The obtained heterogeneous catalysts were characterized by Fourier trans- form infrared (FT-IR), UV-Vis, and inductively coupled plasma (ICP) spectroscopy, scanning electron microscopy (SEM), energy-dispersive X-ray (EDX), and thermogravi- metric analysis (TGA) techniques. Their catalytic activity as biomimetic catalysts was investigated for the selective oxidation of primary and secondary benzylic alcohols to the corresponding carbonyl compounds with t-butylhydro- peroxide as oxidant. SF-3-APTS-Fe(TClPP)Cl demonstrated higher catalytic activity than SF-3-APTS-Mn(TClPP)Cl and SF-3-APTS-Co(TClPP)OAc. The presence of electron- withdrawing substituents on benzylic alcohols enhances the rate of catalytic oxidation. SF-3-APTS-Fe(TClPP)Cl could be reused at least four times without significant loss of its cata- lytic activity.
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