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Molecules 2015, 20(10), 19203-19220; doi:10.3390/molecules201019203

Greener Selective Cycloalkane Oxidations with Hydrogen Peroxide Catalyzed by Copper-5-(4-pyridyl)tetrazolate Metal-Organic Frameworks

1
Chemical Engineering Departament, Instituto Superior de Engenharia de Lisboa, Instituto Politécnico de Lisboa, R. Conselheiro Emídio Navarro, 1959-007 Lisboa, Portugal
2
Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal
3
Department of Chemistry, School of Basic Sciences, Indian Institute of Technology Indore, IET-DAVV Campus, Khandwa Road, Indore 452017, India
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Maxim L. Kuznetsov
Received: 25 September 2015 / Revised: 13 October 2015 / Accepted: 16 October 2015 / Published: 21 October 2015
(This article belongs to the Special Issue Metal Mediated Activation of Small Molecules)
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Abstract

Microwave assisted synthesis of the Cu(I) compound [Cu(µ4-4-ptz)]n [1, 4-ptz = 5-(4-pyridyl)tetrazolate] has been performed by employing a relatively easy method and within a shorter period of time compared to its sister compounds. The syntheses of the Cu(II) compounds [Cu33-4-ptz)42-N3)2(DMF)2]n∙(DMF)2n (2) and [Cu(µ2-4-ptz)2(H2O)2]n (3) using a similar method were reported previously by us. MOFs 1-3 revealed high catalytic activity toward oxidation of cyclic alkanes (cyclopentane, -hexane and -octane) with aqueous hydrogen peroxide, under very mild conditions (at room temperature), without any added solvent or additive. The most efficient system (2/H2O2) showed, for the oxidation of cyclohexane, a turnover number (TON) of 396 (TOF of 40 h−1), with an overall product yield (cyclohexanol and cyclohexanone) of 40% relative to the substrate. Moreover, the heterogeneous catalytic systems 13 allowed an easy catalyst recovery and reuse, at least for four consecutive cycles, maintaining ca. 90% of the initial high activity and concomitant high selectivity. View Full-Text
Keywords: efficient cycloalkane oxidation; reusable heterogeneous catalysts; Cu(I or II) MOFs; microwave; solvent-free; green oxidation efficient cycloalkane oxidation; reusable heterogeneous catalysts; Cu(I or II) MOFs; microwave; solvent-free; green oxidation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Martins, L.; Nasani, R.; Saha, M.; Mobin, S.; Mukhopadhyay, S.; Pombeiro, A. Greener Selective Cycloalkane Oxidations with Hydrogen Peroxide Catalyzed by Copper-5-(4-pyridyl)tetrazolate Metal-Organic Frameworks. Molecules 2015, 20, 19203-19220.

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