Polymer ionic liquid network: a highly effective reusable catalyst for one-pot synthesis of heterocyclic compounds

Abstract

Significant efforts have been devoted to developing immobilized chiral catalysts with high activity, selectivity, and stability. In this present study, a new heterogeneous proline catalyst system was prepared based on strong noncovalent interactions between polymer ionic liquid (PIL) and L-proline. First, pyridine PILs, which can complex with L-proline monomers through noncovalent interactions, were synthesized using reversible addition–fragmentation chain transfer (RAFT) polymerization. The polymer network-supported chiral catalysts were obtained following further free radical polymerization. Different structures were formed in response to different ratios of PIL and chiral monomer, as well as different PIL anions, in the reactions. The new formed layer structures and synergic effects of PIL resulted in heterogeneous catalysts with high catalytic activity and enantioselectivity, thus endowing them with better catalytic performance for the one-pot synthesis of heterocyclic compounds compared to homogeneous catalytic systems. These catalytic systems were able to be reused and recycled five times with no discernible loss in catalytic activity and enantioselectivity. L-Proline was efficiently loaded onto the polymer network simply based on supramolecular interactions, providing a novel method of synthesizing high performance supported catalysts for organic reactions.