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Published on: June 28, 2018
Aromatic donor-acceptor interaction promoted catalyst assemblies for hydrolytic kinetic resolution of epichlorohydrin
Daniel R Blechschmidt1, Matthew D Woodhouse, Sebastien Inagaki
1Department of Chemistry, Northern Michigan University, 1401 Presque Isle Ave., Marquette, MI 49855, USA. jliang@nmu.edu liuyu@nmu.edu.
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.
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