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

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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.

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

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Publication details

The article was received on 11 Sep 2018, accepted on 30 Nov 2018 and first published on 03 Dec 2018


Article type: Paper
DOI: 10.1039/C8OB02249F
Citation: Org. Biomol. Chem., 2019, Advance Article
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    Aromatic donor–acceptor interaction promoted catalyst assemblies for hydrolytic kinetic resolution of epichlorohydrin

    D. R. Blechschmidt, M. D. Woodhouse, S. Inagaki, M. Whitfield, A. Ogunsanya, A. Yoder, D. Lilly, E. W. Heim, L. N. Soucie, J. Liang and Y. Liu, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB02249F

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