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

Erica C M Ording-Wenker; Maxime A Siegler; Martin Lutz; Elisabeth Bouwman

doi:10.1039/c5dt01041a

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

Erica C M Ording-Wenker, Maxime A Siegler, Martin Lutz, Elisabeth Bouwman

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Abstract

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.

Original language	English
Pages (from-to)	12196-209
Number of pages	14
Journal	Dalton Transactions
Volume	44
Issue number	27
DOIs	https://doi.org/10.1039/c5dt01041a
Publication status	Published - 21 Jul 2015

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title = "Catalytic catechol oxidation by copper complexes: development of a structure-activity relationship",

abstract = "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.",

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doi = "10.1039/c5dt01041a",

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volume = "44",

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T1 - Catalytic catechol oxidation by copper complexes

T2 - development of a structure-activity relationship

AU - Ording-Wenker, Erica C M

AU - Siegler, Maxime A

AU - Lutz, Martin

AU - Bouwman, Elisabeth

PY - 2015/7/21

Y1 - 2015/7/21

N2 - 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.

AB - 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.

U2 - 10.1039/c5dt01041a

DO - 10.1039/c5dt01041a

M3 - Article

C2 - 25869395

SN - 1477-9226

VL - 44

SP - 12196

EP - 12209

JO - Dalton Transactions

JF - Dalton Transactions

IS - 27

ER -

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

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