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Issue 33, 2015
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MnII and CuII complexes with arylhydrazones of active methylene compounds as effective heterogeneous catalysts for solvent- and additive-free microwave-assisted peroxidative oxidation of alcohols

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Abstract

A one-pot template reaction of sodium 2-(2-(dicyanomethylene)hydrazinyl)benzenesulfonate (NaHL1) with water and manganese(II) acetate tetrahydrate led to the mononuclear complex [Mn(H2O)6](HL1a)2·4H2O (1), where (HL1a) = 2-(SO3)C6H4(NH)N[double bond, length as m-dash]C(C[triple bond, length as m-dash]N) (CONH2) is the carboxamide species derived from nucleophilic attack of water on a cyano group of (HL1). The copper tetramer [Cu4(H2O)10(1κN2OO,2κNO-L2)2]·2H2O (2) was obtained from reaction of Cu(NO3)2·2.5H2O with sodium 5-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)-4-hydroxybenzene-1,3-disulfonate (Na2H2L2). Both complexes were characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray diffraction. They exhibit a high catalytic activity for the solvent- and additive-free microwave (MW) assisted oxidation of primary and secondary alcohols with tert-butylhydroperoxide, leading to yields of the oxidized products up to 85.5% and TOFs up to 1.90 × 103 h−1 after 1 h under low power (5–10 W) MW irradiation. Moreover, the heterogeneous catalysts are easily recovered and reused, at least for three consecutive cycles, maintaining 89% of the initial activity and a high selectivity.

Graphical abstract: MnII and CuII complexes with arylhydrazones of active methylene compounds as effective heterogeneous catalysts for solvent- and additive-free microwave-assisted peroxidative oxidation of alcohols

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Publication details

The article was received on 11 Feb 2015, accepted on 04 Mar 2015 and first published on 05 Mar 2015


Article type: Paper
DOI: 10.1039/C5RA02667A
Citation: RSC Adv., 2015,5, 25979-25987
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    MnII and CuII complexes with arylhydrazones of active methylene compounds as effective heterogeneous catalysts for solvent- and additive-free microwave-assisted peroxidative oxidation of alcohols

    K. T. Mahmudov, M. Sutradhar, L. M. D. R. S. Martins, M. F. C. Guedes da Silva, A. Ribera, A. V. M. Nunes, S. I. Gahramanova, F. Marchetti and A. J. L. Pombeiro, RSC Adv., 2015, 5, 25979
    DOI: 10.1039/C5RA02667A

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