Facile synthesis of hairy microparticle-/nanoparticle-supported MacMillan and its application to Diels–Alder reaction in water

Abstract

Herein, a series of hairy microparticle-/nanoparticle-supported MacMillan was successfully synthesized by RAFT precipitation polymerization combination with surface-initiated RAFT polymerization. The research’s interest was aimed at achieving a significant enhancement of the catalytic performance which was achieved due to the changes of the polymer particle size, the molecular weight of the grafting polymer brushes, as well as the grafting polymer structure. The results showed that nanoeffect was the key to affect the catalytic activity and selectivity of catalyst system. The hairy nanoparticle had good dispersion in the reaction media and exhibited better catalytic activity and selectivity than hairy microspheres. In addition, the brush structure can be modified by grafting copolymerization with acrylamide which had the synergistic effect to effectively promote the catalyst reaction. The more significant advantages of the hairy nanoparticle-supported MacMillan were that it can effectively catalyze a representative asymmetric Diels–Alder reaction between cyclopentadiene and cinnamaldehyde in pure water and can be recycled five times while maintaining activity and selectivity.