A Mild Catalytic Oxidation System: FePcOTf/H2O2 Applied for Cyclohexene Dihydroxylation.

Baocheng Zhou,Wenxing Chen

doi:10.3390/molecules20058429

Baocheng Zhou, Wenxing Chen

Open Access

https://doi.org/10.3390/molecules20058429

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Journal: Molecules (Basel, Switzerland)	Publication Date: May 11, 2015
Citations: 40	License type: CC BY 4.0

Affiliation: Zhejiang Sci-Tech University

Abstract

Iron (III) phthalocyanine complexes were employed for the first time as a mild and efficient Lewis acid catalyst in the selective oxidation of cyclohexene to cyclohexane-1,2-diol. It was found that the catalyst FePcOTf shown excellent conversion and moderate selectivity relative to other iron (III) phthalocyanine complexes. The optimum conditions of the oxidation reaction catalyzed by FePcOTf/H2O2 have been researched in this paper. Iron (III) phthalocyanine triflate (1 mol %) as catalyst, hydrogen peroxide as oxidant, methanol as solvent, and a mole ratio of substrate and oxidant (H2O2) of 1:1 were used for achieving moderate yields of 1,2-diols under reflux conditions after eight hours.

Highlights

In 1988, Sharpless and Jacobsen developed the OsO4/N-methylmorpholine N-oxide (NMO)oxidation system using cinchona alkaloid derivatives as chiral ligands for the asymmetric dihydroxylation of alkenes to obtain 1,2-diols [1]. 1,2-Diols are useful building blocks in the design of pharmaceuticals [2] and natural product synthesis [3]
We examined the oxidation of cyclohexene with H2O2 using FePcX [23] as the catalyst
The iron (III) phthalocyanine catalyzed the oxidation of cyclohexene with H2O2

Summary

Introduction

In 1988, Sharpless and Jacobsen developed the OsO4/N-methylmorpholine N-oxide (NMO)oxidation system using cinchona alkaloid derivatives as chiral ligands for the asymmetric dihydroxylation of alkenes to obtain 1,2-diols [1]. 1,2-Diols are useful building blocks in the design of pharmaceuticals [2] and natural product synthesis [3]. 1,2-Diols are useful building blocks in the design of pharmaceuticals [2] and natural product synthesis [3]. These compounds can be synthesized from alkenes through alkene dihydroxylation [4]. The industrial use of OsO4 is restricted on account of its expensive price and toxic properties. Several catalysts such as polyoxometalates [11,12], sodium tungstate [13], MgxFe3-xO4 complex oxide [14], peroxovanadium [15] and oxorhenium [16] have been developed. The selective dihydroxylation of olefins with high efficiency in terms of the amount of H2O2 is difficult to achieve

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Results

Conclusion