Functionalized Ionic (Poly)Styrenes and their Application as Catalysts in the Cycloaddition of CO2 to Epoxides

Valorization of CO2, an abundant C(1) synthon, into platform chemicals is of growing interest. In this context, a key reaction is the cycloaddition of CO2 to epoxides to form carbonates (CCE). A series of organocatalysts for this reaction, based on imidazolium salts modified with a styrene functional group and a second variable functional group, were prepared and characterized. Both the ionic salts and ionic polymers derived from the salts were evaluated in this reaction. In general, the monomers perform slightly better than the polymers; however, the latter are considerably more convenient to use. Of the catalysts studied, the ionic polystyrene imidazolium salt with an ammonium functionality shows highest activity, tolerates a range of epoxides, and can be recycled multiple times without loss of activity.