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Bifunctional silanol-based HBD catalysts for CO2 fixation into cyclic carbonates

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Abstract

First examples of unprecedented silanol-based bifunctional HBD catalysts [(tBuO)2{(N(CH2CH2)3N)CH2CH2O}Si(OH)]+I and (Rac)- and (R)-[(tBuO)2{(N(CH2CH2)3N)CH2(Et)CHO)}Si(OH)]+I with tetraalkylammonium units directly incorporated into their structures were prepared from tailor-made silanols. These bifunctional silanols were used together with other mixed alkoxysilanols of general formula (tBuO)2(RO)SiOH (R = Me, Et, iPr, –CH2CH2I and –CH(Et)CH2I) in a systematic study of their catalytic properties for the preparation of cyclic carbonates using a library of epoxides and industrial-grade carbon dioxide. With 4 mol% catalyst loading in the absence of a solvent and an external nucleophile source, the bifunctional catalysts showed good to very good conversion of epoxides to the corresponding cyclic carbonates within 10 h at 70 °C and 75 psi of CO2. Furthermore, the developed synthetic approach used in the preparation of these mixed alkyl silanols via the hydrolysis of the corresponding acetoxysilyl alkoxides (tBuO)2(RO)Si(OAc) (R = organic moiety) allowed a straightforward route to the modification of the steric bulk around the silicon atom and the introduction of functional groups for further derivatization.

Graphical abstract: Bifunctional silanol-based HBD catalysts for CO2 fixation into cyclic carbonates

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Publication details

The article was received on 24 Sep 2019, accepted on 04 Nov 2019 and first published on 05 Nov 2019


Article type: Paper
DOI: 10.1039/C9NJ04840E
New J. Chem., 2019, Advance Article

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    Bifunctional silanol-based HBD catalysts for CO2 fixation into cyclic carbonates

    J. Pérez-Pérez, U. Hernández-Balderas, D. Martínez-Otero and V. Jancik, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ04840E

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