Aromatic donor–acceptor interaction promoted catalyst assemblies for hydrolytic kinetic resolution of epichlorohydrin

Abstract

Three generations of Co(III)–salen complexes containing electron-deficient aromatic moieties (acceptors) have been synthesized. When electron-rich aromatic compounds (donors) were introduced, these complexes were designed to form catalyst assemblies through aromatic donor–acceptor interaction. For all three generations of complexes, the addition of a proper donor led to higher catalytic efficiency in the hydrolytic kinetic resolution (HKR) of epichlorohydrin. The reaction rates are in the following order: Generation 3 > Generation 2 > Generation 1. The aromatic donor–acceptor interaction was verified by NMR spectroscopy and UV-vis absorption spectroscopy studies. These results demonstrated that aromatic donor–acceptor interaction can be a valuable driving force in the assembly of supramolecular catalysts.