Low Antimicrobial Toxicity Ionic Liquids: Solvents for Asymmetric Carbonyl-Ene Reactions of Phenylglyoxal

Abstract

This work demonstrates that low antimicrobial toxicity C2-substituted imidazolium-based ILs, with either ester or amide groups in the side chain, can successfully replace harmful volatile organic compounds (VOCs) in the asymmetric carbonyl-ene reaction of phenylglyoxal with four alkenes catalysed by {[(R)-BINAP]Pd}(SbF6)2. Furthermore, the Pd(II) catalyst immobilised in these ILs was recycled and reused up to 5 times without loss of enantioselectivity, although a decrease in yield was observed.

Keywords

• antimicrobial toxicity
• asymmetric catalysis
• carbonyl-ene reaction
• ionic liquids