Bifunctional Onium and Potassium Iodides as Nucleophilic Catalysts for the Solvent-Free Syntheses of Carbonates, Thiocarbonates, and Oxazolidinones from Epoxides.

Abstract

The catalytic potential of organo-onium iodides as nucleophilic catalysts is aptly demonstrated in the synthesis of cyclic carbonates from epoxides and carbon dioxide (CO2 ), as a representative CO2 utilization reaction. Although organo-onium iodide nucleophilic catalysts are metal-free environmentally benign catalysts, harsh reaction conditions are generally required to efficiently promote the coupling reactions of epoxides and CO2 . To solve this problem and accomplish efficient CO2 utilization reactions under mild conditions, bifunctional onium iodide nucleophilic catalysts bearing a hydrogen bond donor moiety were developed by our research group. Based on the successful bifunctional design of the onium iodide catalysts, nucleophilic catalysis using a potassium iodide (KI)-tetraethylene glycol complex was also investigated in coupling reactions of epoxides and CO2 under mild reaction conditions. These effective bifunctional onium and potassium iodide nucleophilic catalysts were applied to the solvent-free syntheses of 2-oxazolidinones and cyclic thiocarbonates from epoxides.