Fe3O4@dopa (dopa = dopamine hydrochloride) functionalized Mn(III) Schiff base complex: A promising magnetically separable heterogeneous catalyst for oxidative transformations

Abstract

A chiral Schiff base complex has been prepared by treating (R)-1,2-diaminopropane with 3,5-dichlorosalicylaldehyde in ethanol, followed by addition of manganese chloride hexahydrate to generate a homogeneous catalyst, [MnL(Cl)(H2O)] (HMN). Crystal structure of the complex reveals its mononuclear nature. Circular dichroism (CD) studies indicate that the ligand and its corresponding complex contain an asymmetric center. The catalytic activity of HMN toward epoxidation of alkenes, oxidation of alcohols and oxidation of alkanes has been investigated in the presence of iodosylbenzenediacetate (PhI(OAc)2), in acetonitrile. In the present work we found yields to be much higher compared to our previous approaches. For further adaptation, we attached our efficient homogeneous catalyst with surface modified magnetic nanoparticles (Fe3O4@dopa) and thereby obtained a new magnetically separable nanocatalyst Fe3O4@dopa@MnLCl (FDM). This catalyst has been characterized and its oxidation ability assessed in similar conditions as those used for the homogeneous catalyst. Enantiomeric excess in epoxide yield reveals retention of chirality of the active site of Fe3O4@dopa@MnLCl. The catalyst can be recovered by magnetic separation and recycled several times without significant loss of catalytic activity.