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Selective cyclohexene oxidation to allylic compounds over a Cu-triazole framework <i>via</i> homolytic activation of hydrogen peroxide

Panyapat Ponchai, Kanyaporn Adpakpang, Sareeya Bureekaew

2021Dalton Transactions13 citationsDOI

Abstract

Utilization of metal-organic frameworks as heterogeneous catalysts is crucial owing to their abundant catalytic sites and well-defined porous structures. Highly robust [Cu3(trz)3(μ3-OH)(OH)2(H2O)4]·2H2O (trz = 1,2,4-triazole) was employed as a catalyst for liquid-phase cyclohexene oxidation with hydrogen peroxide (H2O2). Possessing the porous structure together with Lewis acid attributes from the triangular [Cu3(trz)3(μ3-OH)] center, selective oxidation of cyclohexene to allylic products gives a molar yield of 31% with 87% selectivity. According to the highly selective allylic production, the reaction over the present Cu-MOF plausibly occurs via homolytic activation of H2O2. This finding elucidates the unique features of the MOF for efficient catalysis of cyclohexene oxidation.

Topics & Concepts

Allylic rearrangementHomolysisCyclohexeneChemistryHydrogen peroxideCatalysisSelectivityLewis acids and basesMetalPhotochemistryPeroxideCombinatorial chemistryOrganic chemistryRadicalMetal-Organic Frameworks: Synthesis and ApplicationsCatalytic Processes in Materials ScienceCovalent Organic Framework Applications