Catalytic catechol oxidation by copper complexes: development of a structure-activity relationship

A large library of Cu(II) 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...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2015-07, Vol.44 (27), p.12196-12209
Main Authors: Ording-Wenker, Erica C M, Siegler, Maxime A, Lutz, Martin, Bouwman, Elisabeth
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Catechol
Catechols - chemistry
Chloride ions
Coordination Complexes - chemistry
Copper - chemistry
Copper compounds
Crystallography, X-Ray
Ligands
Molecular Structure
Oxidation
Oxidation-Reduction
X-rays
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Summary:A large library of Cu(II) 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 Cu(II) 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.
ISSN:1477-9226
1477-9234
DOI:10.1039/c5dt01041a