Copper–oxygen adducts: new trends in characterization and properties towards C–H activation

De Tovar, Jonathan; Leblay, Rébecca; Wang, Yongxing; Wojcik, Laurianne; Thibon-Pourret, Aurore; Réglier, Marius; Simaan, A. Jalila; Le Poul, Nicolas; Belle, Catherine

doi:10.1039/d4sc01762e

Chem. Sci.

2024

DOI: 10.1039/d4sc01762e

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Copper–oxygen adducts: new trends in characterization and properties towards C–H activation

Jonathan De Tovar,

Rébecca Leblay,

Yongxing Wang

et al.

Abstract: This review summarizes the latest discoveries in the field of C−H activation by copper monoxygenases and more particularly by their bioinspired systems. This work first describes recent background on copper-containing...

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Intramolecular Phenolic H-Atom Abstraction by a N₃ArOH Ligand-Supported (μ-η²:η²-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase

Panda,

Phan,

Dunietz

et al. 2024

J. Am. Chem. Soc.

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Synthetic side-on peroxide-bound dicopper(II) ( S P) complexes are important for understanding the active site structure/function of many copper-containing enzymes. This work highlights the formation of new {CuII(μ-η2:η2-O2 2–)CuII} complexes (with electronic absorption and resonance Raman (rR) spectroscopic characterization) using tripodal N3ArOH ligands at −135 °C, which spontaneously participate in intramolecular phenolic H-atom abstraction (HAA). This results in the generation of bis(phenoxyl radical)bis(μ-OH)dicopper(II) intermediates, substantiated by their EPR/UV–vis/rR spectroscopic signatures and crystal structural determination of a diphenoquinone dicopper(I) complex derived from ligand para-CC coupling. The newly observed chemistry in these ligand–Cu systems is discussed with respect to (a) our Cu-MeAN (tridentate N,N,N′,N′,N″-pentamethyldipropylenetriamine)-derived model S P species, which was unreactive toward exogenous monophenol addition (J. Am. Chem. Soc. 2012, 134, 8513–8524), emphasizing the impact of intramolecularly tethered ArOH groups, and (b) recent advances in understanding the mechanism of action of the tyrosinase (Ty) enzyme.

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Intramolecular Phenolic H-Atom Abstraction by a N₃ArOH Ligand-Supported (μ-η²:η²-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase

Panda,

Phan,

Dunietz

et al. 2024

J. Am. Chem. Soc.

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Copper–oxygen adducts: new trends in characterization and properties towards C–H activation

Abstract: This review summarizes the latest discoveries in the field of C−H activation by copper monoxygenases and more particularly by their bioinspired systems. This work first describes recent background on copper-containing...

Cited by 1 publication

References 305 publications

Intramolecular Phenolic H-Atom Abstraction by a N₃ArOH Ligand-Supported (μ-η²:η²-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase

Intramolecular Phenolic H-Atom Abstraction by a N₃ArOH Ligand-Supported (μ-η²:η²-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase

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Copper–oxygen adducts: new trends in characterization and properties towards C–H activation

Abstract: This review summarizes the latest discoveries in the field of C−H activation by copper monoxygenases and more particularly by their bioinspired systems. This work first describes recent background on copper-containing...

Cited by 1 publication

References 305 publications

Intramolecular Phenolic H-Atom Abstraction by a N3ArOH Ligand-Supported (μ-η2:η2-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase

Intramolecular Phenolic H-Atom Abstraction by a N3ArOH Ligand-Supported (μ-η2:η2-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase

Contact Info

Product

Resources

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Intramolecular Phenolic H-Atom Abstraction by a N₃ArOH Ligand-Supported (μ-η²:η²-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase

Intramolecular Phenolic H-Atom Abstraction by a N₃ArOH Ligand-Supported (μ-η²:η²-Peroxo)dicopper(II) Species Relevant to the Active Site Function of oxy-Tyrosinase