Issue 47, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Sept. 2019
Accepted
04 Nov. 2019
First published
05 Nov. 2019

New J. Chem., 2019,43, 18525-18533

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, 43, 18525 DOI: 10.1039/C9NJ04840E

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