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Issue 81, 2016
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A sulfonated Schiff base dimethyltin(IV) coordination polymer: synthesis, characterization and application as a catalyst for ultrasound- or microwave-assisted Baeyer–Villiger oxidation under solvent-free conditions

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Abstract

The synthesis and crystal structure of the new dimethyltin(IV) compound [SnMe2(HL)(CH3OH)]n·(0.5nCH3OH) (1) derived from the Schiff base 2-[(2,3-dihydroxyphenyl)methylideneamino]benzenesulfonic acid (H3L) are described. Despite having six potentially donating centres (one imine nitrogen, two phenoxo and three sulfonate oxygen atoms), the monoprotonated dianionic ligand (HL2−) behaves as an O,O,O-tridentate chelator. Single crystal X-ray diffraction revealed that 1 is a 1D coordination polymer with every tin(IV) ion bound to two methyl groups, a methanol molecule, two Ophenoxo and one μ-Osulfonate atom from HL2−. The coordination polymer 1 was applied as a heterogeneous catalyst for the Baeyer–Villiger oxidation of ketones to esters or lactones, using aqueous hydrogen peroxide as oxidant, under ultrasound (US) or microwave (MW) irradiation and solvent- and additive-free conditions. Overall conversions up to 76/82, 98/93, 93/89, 91/94, 83/90, 68/62 and 81/87% under US/MW irradiations were obtained with 3,3-dimethyl-2-butanone, cyclopentanone, 2-methylcyclopentanone, cyclohexanone, 3-methylcyclohexanone, benzophenone and acetophenone, respectively. The catalyst can be recycled up to five cycles without losing appreciable activity.

Graphical abstract: A sulfonated Schiff base dimethyltin(iv) coordination polymer: synthesis, characterization and application as a catalyst for ultrasound- or microwave-assisted Baeyer–Villiger oxidation under solvent-free conditions

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Publication details

The article was received on 06 Jun 2016, accepted on 11 Aug 2016 and first published on 12 Aug 2016


Article type: Paper
DOI: 10.1039/C6RA14689A
Citation: RSC Adv., 2016,6, 78225-78233
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    A sulfonated Schiff base dimethyltin(IV) coordination polymer: synthesis, characterization and application as a catalyst for ultrasound- or microwave-assisted Baeyer–Villiger oxidation under solvent-free conditions

    L. M. D. R. S. Martins, S. Hazra, M. F. C. Guedes da Silva and A. J. L. Pombeiro, RSC Adv., 2016, 6, 78225
    DOI: 10.1039/C6RA14689A

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