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Simultaneous Activation of Carbon Dioxide and Epoxides to Produce Cyclic Carbonates by Cross‐linked Epoxy Resin Organocatalysts

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Using crossed-linked epoxy resin catalysts, cyclic carbonates were synthesized via simultaneous activation of carbon dioxide and epoxides. A detailed description of the mechanism for the simultaneous activation of carbon dioxide and epoxides is proposed and certified on the basis of the intensive investigations on intermolecular interactions and key intermediates.


Abstract

The development of efficient bifunctional organocatalysts for the catalytic conversion of CO2 under mild conditions remains particularly challenging. Inspired by the synergistic mechanism of intramolecular Lewis acid-base active sites, we report a series of bifunctional cross-linked epoxy resin organocatalysts containing multiple active sites for the cycloaddition reaction of dilute CO2 with epoxides. These catalysts exhibit high reactivity and product selectivity (10 examples, >99 %) for the cycloaddition reactions of a variety of epoxides and CO2, and surprisingly, epichlorohydrin (ECH), can be converted under ambient temperature and pressure (25 °C, 1.0 bar) without co-catalysts. 1H NMR, 13C NMR, 19F NMR and in situ IR studies suggest that the simultaneous and efficient activation of CO2 and epoxides is responsible for the improved catalytic activity. Upon an insightful investigation of the catalytic mechanism, this protocol will contribute to the development of efficient and environmentally friendly metal-free catalysts.

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