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Issue 27, 2015
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Catalytic catechol oxidation by copper complexes: development of a structure–activity relationship

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Abstract

A large library of CuII complexes with mononucleating and dinucleating ligands was synthesized to investigate their potential as catalysts for the catalytic oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC). X-ray structure determination for a number of these complexes revealed relatively large Cu⋯Cu distances and the formation of polymeric species. Comparison of the 3,5-DTBC oxidation rates showed that ligands that stabilize the biomimetic dinuclear CuII μ-thiolate complex also result in copper compounds that are much more active in the oxidation of 3,5-DTBC. This oxidation activity is however inhibited by the presence of chloride ions. The highest kcat that was observed was 6900 h−1, which is one of the highest turnover frequencies reported so far for catechol oxidation in CH3CN.

Graphical abstract: Catalytic catechol oxidation by copper complexes: development of a structure–activity relationship

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Publication details

The article was received on 16 Mar 2015, accepted on 07 Apr 2015 and first published on 07 Apr 2015


Article type: Paper
DOI: 10.1039/C5DT01041A
Author version available: Download Author version (PDF)
Citation: Dalton Trans., 2015,44, 12196-12209
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    Catalytic catechol oxidation by copper complexes: development of a structure–activity relationship

    E. C. M. Ording-Wenker, M. A. Siegler, M. Lutz and E. Bouwman, Dalton Trans., 2015, 44, 12196
    DOI: 10.1039/C5DT01041A

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