Copper-mediated hydroxylation of an arene:  kinetics and mechanism of the reaction of a dicopper(II) m-xylyl-containing complex with H2O2 to yield a phenoxodicopper(II) complex

Cruse, Richard W.; Kaderli, Susan; Meyer, Charles J.; Zuberbuehler, Andreas D.; Karlin, Kenneth D.

doi:10.1021/ja00223a020

Cited by 38 publications

(32 citation statements)

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“…357 A (1,1-hydroperoxo)dicopper complex was identified at low temperature as an intermediate in the double hydroxylation of the bridging arene in L58b upon reaction of its dicopper(II) complex with H 2 O 2 , 358 a reaction reminiscent of an earlier report of the system supported by L49a . 361 …”

Section: Dicopper Compoundsmentioning

confidence: 99%

Copper–Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity

et al. 2017

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A longstanding research goal has been to understand the nature and role of copper–oxygen intermediates within copper-containing enzymes and abiological catalysts. Synthetic chemistry has played a pivotal role in highlighting the viability of proposed intermediates and expanding the library of known copper–oxygen cores. In addition to the number of new complexes that have been synthesized since the previous reviews on this topic in this journal (Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013–1046 and Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047–1076), the field has seen significant expansion in the (1) range of cores synthesized and characterized, (2) amount of mechanistic work performed, particularly in the area of organic substrate oxidation, and (3) use of computational methods for both the corroboration and prediction of proposed intermediates. The scope of this review has been limited to well-characterized examples of copper–oxygen species but seeks to provide a thorough picture of the spectroscopic characteristics and reactivity trends of the copper–oxygen cores discussed.

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Section: Dicopper Compoundsmentioning

confidence: 99%

Copper–Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity

et al. 2017

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“…Moreover, it is also consistent with the proposed involvement of three or four Cu atoms in a xylyl hydroxylation reaction in which a (μ‐1,1‐hydroperoxide) dicopper intermediate is further activated by a second dicopper center that acts as a Lewis acid thus promoting the electrophilic character of the hydroperoxide towards the substrate 2e. 13…”

Section: Peroxidative Oxidation Of Cyclohexane Catalyzed By Complexesmentioning

confidence: 99%

Multinuclear Copper Triethanolamine Complexes as Selective Catalysts for the Peroxidative Oxidation of Alkanes under Mild Conditions

Kirillov¹,

Kopylovich²,

Kirillova³

et al. 2005

Angew Chem Int Ed

257

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Copper species are widely found in nature and are present in many enzymes as di-, tri-or polynuclear Cu centers that catalyze selectively various oxidation reactions.[1] These reactions include the poorly characterized particulate methane monooxygenase (pMMO), which is present in methanotrophs, wherein a tri-or multinuclear Cu cluster catalyzes alkane hydroxylation and alkene epoxidation.[1f-i] Although increasing attention has been paid to the design of Cu complexes with polydentate ligands as models of copper oxidases [1a,b, 2] and some mononuclear compounds have been

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“…For the synthesis, see: Ghosh & Mukherjee (1998). For the monooxygenase activity of the dicopper(I) complexes of the title compound, see: Cruse et al (1988); Karlin et al (1984). V = 2757.6 (9) Å 3 Z = 4 Mo K radiation = 0.29 mm À1 T = 296 (2) K 0.45 Â 0.34 Â 0.12 mm…”

Section: Related Literaturementioning

confidence: 99%

N,N′-Dimethyl-N,N′-bis[2-(2-pyridyl)ethyl](p-phenylenedimethylene)diammonium bis(perchlorate)

Yisgedu¹,

Tesema²,

Gultneh³

et al. 2007

Acta Cryst E

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In the title compound, C24H32N42+·2ClO4−, the two N atoms of the amine are protonated. The H atoms of the protonated amine form hydrogen bonds with the pyridyl N atoms (intramolecular) and O atoms of adjacent perchlorate anions. In addition, there are weak C—H...O interactions which link the formula units into chains along [101]. Each perchlorate anion is disordered over three conformations, with occupancy factors of 0.482 (2), 0.331 (2) and 0.187 (4), and 0.532 (8), 0.324 (4) and 0.133 (7).

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Copper-mediated hydroxylation of an arene: kinetics and mechanism of the reaction of a dicopper(II) m-xylyl-containing complex with H2O2 to yield a phenoxodicopper(II) complex

Cited by 38 publications

References 0 publications

Copper–Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity

Copper–Oxygen Complexes Revisited: Structures, Spectroscopy, and Reactivity

Multinuclear Copper Triethanolamine Complexes as Selective Catalysts for the Peroxidative Oxidation of Alkanes under Mild Conditions

N,N′-Dimethyl-N,N′-bis[2-(2-pyridyl)ethyl](p-phenylenedimethylene)diammonium bis(perchlorate)

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