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Microwave-assisted one-pot functionalization of metal-organic framework MIL-53(Al)-NH2 with copper(II) complex and its application in olefin oxidation

Abstract

A simple, rapid, and efficient functionalization of the metal-organic framework MIL-53(Al)-NH2 with copper(II) complex by microwave irradiation is described. The one-pot postsynthetic modification was based on the Schiff base reaction between aldehyde added and primary aryl amino group in the organic linker of MIL-53(Al)-NH2, which afforded coordination sites for copper(II). The effects of synthetic parameters such as solvent, reaction time, and reactant ratio were evaluated. The functionalized materials were structurally characterized and examined for potential applications in catalysis. The copper complex functionalized MIL-53(Al) was active towards the oxidation of olefins with tert-butyl hydroperoxide as an oxidant. The results showed that if the olefin possessed allylic hydrogen such as cyclohexene, allylic oxidation products were obtained, but epoxide was the major product obtained from terminal olefin without allylic hydrogen. The reaction mechanism based on Density Functional Theory calculations provides some insights on the observed experimental results.

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Publication details

The article was received on 21 Sep 2017, accepted on 10 Nov 2017 and first published on 13 Nov 2017


Article type: Paper
DOI: 10.1039/C7CY01941F
Citation: Catal. Sci. Technol., 2017, Accepted Manuscript
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    Microwave-assisted one-pot functionalization of metal-organic framework MIL-53(Al)-NH2 with copper(II) complex and its application in olefin oxidation

    T. Bunchuay, R. Ketkaew, P. Chotmongkolsap, T. Chutimasakul, J. Kanarat, Y. Tantirungrotechai and J. Tantirungrotechai, Catal. Sci. Technol., 2017, Accepted Manuscript , DOI: 10.1039/C7CY01941F

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