Monodentate H-bond donor bifunctional catalyst in fixation of atmospheric pressure carbon dioxide into cyclic carbonates

Abstract

The efficient conversion of epoxides and CO2 into cyclic carbonates by employing H-bond donor (HBD) and nucleophilic halide cooperating catalysis under mild conditions is an attractive research topic. Herein, we report a new onium halide bearing a CON(H) moiety as a weak HBD catalyst to facilitate the cycloaddition reaction of epoxides and CO2 under mild conditions. The structural influences on the catalytic activity were scrutinized, which included tunable substituents, the distance between functional groups, and counter anions. The result indicated that the catalyst of the bis-meta-substitutions on an aromatic ring exhibited excellent activity for converting epichlorohydrin into cyclic carbonate under atmospheric pressure at 25–70 °C. Twelve terminal epoxides were converted into corresponding cyclic carbonates in 72–99 % isolated yield. A reasonable activation mechanism was proposed and validated by using control experiments and NMR titrations. In addition, the good recyclability proves that the onium halide is a sustainable green organocatalyst.