Copper(II) complexes of bidentate ligands containing nitrogen and sulfur donors: Synthesis, structures, electrochemistry and catalytic properties

Malachowski, Mitchell R.; Adams, Mark E.; Murray, Daniel; White, Raymond P.; Elia, Nadia; Rheingold, Arnold L.; Zakharov, Lev N.; Kelly, Richard S.

doi:10.1016/j.ica.2008.06.008

Cited by 15 publications

(8 citation statements)

References 26 publications

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“…Among different examples of sophisticated and complex ligands used in the copper chemistry, N ‐heterocyclic carbenes became a good choice for the performance of various catalytic transformations in a simple and efficient way . In particular, the NHC copper complexes that contained both: the aryl and alkyl groups with different heteroatoms became an interesting alternative for the traditional well‐known catalytic systems . To date, a few groups have reported structures of the NHC copper complexes containing mixed ligands with a sulfur moiety .…”

Section: Introductionmentioning

confidence: 99%

NHC copper complexes functionalized with sulfoxide and sulfone moieties

Szadkowska

Pawłowski

Zaorska

et al. 2019

Applied Organom Chemis

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A series of N-heterocyclic copper carbene complexes bearing sulfoxide and sulfone moieties have been prepared. In case of new copper compounds with sulfone ligand, the solid-state structures were determined using X-Ray crystallography. Obtained complexes were investigated as catalysts in such transformations as: 1,3-dipolar cycloaddition of alkynes and azides (CuAAC), A 3 coupling reaction and β-hydroboration and compared with standard copper catalytic systems.

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Section: Introductionmentioning

confidence: 99%

NHC copper complexes functionalized with sulfoxide and sulfone moieties

Szadkowska

Pawłowski

Zaorska

et al. 2019

Applied Organom Chemis

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“…To date, numerous modifications of the NHC ligands with various substituents and heteroatoms have been reported . However, examples of copper complexes containing together “mixed” alkyl and aryl moieties remain relatively rare . This change in steric crowding of the NHC ligand by replacement of one of the traditional functional groups by a less bulky group can influence the catalyst activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structural Characterization and Catalytic Activities of Sulfur‐Functionalized NHC–Copper(I) Complexes

et al. 2017

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The synthesis of a family of N‐heterocyclic carbene–copper complexes bearing a sulfur moiety by using different copper(I) halides through convenient procedures is reported. The solid‐state structures of the presented copper compounds were elucidated based on X‐ray crystallographic analysis. The obtained complexes were examined in various catalytic transformations including 1,3‐dipolar cycloaddition of alkynes and azides, A3 coupling reaction, and β‐hydroboration.

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“…[27][28][29][30][31][32][33][34][35][36][37][38][39][40] However, a few examples of monocopper complexes with sulfur atoms have been described in the literature. 41,42 They were mainly designed to tune the geometry through forced coordination of thioether groups, thus enhancing electron transfer properties. Despite the fact that they are drifted from modeling biological systems, mononuclear complexes are interesting because their synthesis is easier and allows the modification of their structure in a systematic way, providing a better understanding of the elements favoring their catecholase activity.…”

Section: Introductionmentioning

confidence: 99%

Rate enhancement of the catechol oxidase activity of a series of biomimetic monocopper(ii) complexes by introduction of non-coordinating groups in N-tripodal ligands

et al. 2012

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Asymmetrical N-tripodal ligands have been synthesized in three steps. Diversity has been introduced at the first step of the synthesis by adding pyrazine, pyridine, benzyl and thiophene rings. The corresponding Cu II complexes have been prepared by reaction with CuCl 2 and characterized by Electron Paramagnetic Resonance (EPR), UV-Vis spectroscopies and cyclic voltammetry. The data show that the ligand coordinates to Cu II in a mononuclear fashion in solution and that the complexes display a square pyramidal geometry. All complexes are characterized by a quasi-reversible one-electron redox behavior in acetonitrile. The ability of the complexes to oxidize 3,5-di-tert-butylcatechol to 3,5-di-tert-butylquinone has been studied and the results show that the rate of the reaction depends on the basicity and the steric hindrance of the heterocyclic donor. Best results have been obtained with Cu II complexes coordinated to bidentate ligands, since they facilitate the approach and the coordination of catechol to the metal. Particularly, the introduction of a thiophenyl group to mimic the sulfur atom at proximity to the catalytic center in the catechol oxidase protein structure improves the catalytic activity of the complex.

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Copper(II) complexes of bidentate ligands containing nitrogen and sulfur donors: Synthesis, structures, electrochemistry and catalytic properties

Cited by 15 publications

References 26 publications

NHC copper complexes functionalized with sulfoxide and sulfone moieties

NHC copper complexes functionalized with sulfoxide and sulfone moieties

Synthesis, Structural Characterization and Catalytic Activities of Sulfur‐Functionalized NHC–Copper(I) Complexes

Rate enhancement of the catechol oxidase activity of a series of biomimetic monocopper(ii) complexes by introduction of non-coordinating groups in N-tripodal ligands

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