Cooperative Multifunctional Organocatalysts for Ambient Conversion of Carbon Dioxide into Cyclic Carbonates

Abstract

A series of pincer-type compounds possessing an N-heterocyclic carbene precursor and a carboxyl group as proton transfer agent were synthesized and used as organocatalysts for the cycloaddition of epoxides with CO2. In this context, we have demonstrated the high activity of these one-component organocatalysts in the CO2 transformation to cyclic carbonates under ambient conditions (room temperature, 1 bar of CO2). The catalytic potential of these multifunctional organocatalysts on challenging internal epoxides is particularly deserving of mention because organocatalysts that are able to mediate the cycloaddition reaction of internal epoxides with CO2 under mild conditions remain scarce. The intramolecular synergistic activation mechanism was elucidated by control experiments and DFT calculations.