Issue 89, 2015

Synthesis and bifunctional catalysis of metal nanoparticle-loaded periodic mesoporous organosilicas modified with amino groups

Abstract

The present article describes the development of a periodic mesoporous organosilica (PMO)-based bifunctional catalyst that includes both oxidative and base catalytic activities. Periodic mesoporous ethylenesilica (PME) was selected as a catalyst support and modified with ethylenediamine through epoxidation of bridging ethylene moieties and the following nucleophilic addition in order to construct base sites. FT-IR measurements for the resulting material, PME-ED, reveal the successful introduction of amino groups into the bridging ethylene moieties. PME-ED can promote Knoevenagel condensation between benzaldehyde and various active methylene compounds as a solid base catalyst. The scope of applicable active methylene compounds in this catalytic system shows the base strength of PME-ED, in which a proton can be abstracted from diethyl malonate (pKa: 16.4) but not from benzyl cyanide (pKa: 21.9). Moreover, the generation of bifunctional catalytic properties to promote a one-pot tandem reaction consisting of alcohol oxidation and Knoevenagel condensation is realised by loading of Au nanoparticles within PME-ED. This catalyst design methodology can be also extended to developing another bifunctional catalyst that is composed of Pd nanoparticles and PME modified with N,N-dimethylethylenediamine in order to promote a Tsuji–Trost reaction.

Graphical abstract: Synthesis and bifunctional catalysis of metal nanoparticle-loaded periodic mesoporous organosilicas modified with amino groups

Supplementary files

Article information

Article type
Paper
Submitted
05 Jul 2015
Accepted
21 Aug 2015
First published
21 Aug 2015

RSC Adv., 2015,5, 72653-72658

Synthesis and bifunctional catalysis of metal nanoparticle-loaded periodic mesoporous organosilicas modified with amino groups

Y. Horiuchi, D. Do Van, Y. Yonezawa, M. Saito, S. Dohshi, T. Kim and M. Matsuoka, RSC Adv., 2015, 5, 72653 DOI: 10.1039/C5RA13090E

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