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Catalytic Oxygenation of Hydrocarbons by Mono‐μ‐oxo Dicopper(II) Species Resulting from O−O Cleavage of Tetranuclear Cu <sup>I</sup> /Cu <sup>II</sup> Peroxo Complexes

Ramona Jurgeleit, Benjamin Grimm‐Lebsanft, Benedikt M. Flöser, Melissa Teubner, Sören Buchenau, Laura Senft, Jonas Hoffmann, Maria Naumova, Christian Näther, Ivana Ivanović‐Burmazović, Michael Rübhausen, Felix Tuczek

2021Angewandte Chemie International Edition21 citationsDOIOpen Access PDF

Abstract

Abstract One of the challenges of catalysis is the transformation of inert C−H bonds to useful products. Copper‐containing monooxygenases play an important role in this regard. Here we show that low‐temperature oxygenation of dinuclear copper(I) complexes leads to unusual tetranuclear, mixed‐valent μ 4 ‐peroxo [Cu I /Cu II ] 2 complexes. These Cu 4 O 2 intermediates promote irreversible and thermally activated O−O bond homolysis, generating Cu 2 O complexes that catalyze strongly exergonic H‐atom abstraction from hydrocarbons, coupled to O‐transfer. The Cu 2 O species can also be produced with N 2 O, demonstrating their capability for small‐molecule activation. The binding and cleavage of O 2 leading to the primary Cu 4 O 2 intermediate and the Cu 2 O complexes, respectively, is elucidated with a range of solution spectroscopic methods and mass spectrometry. The unique reactivities of these species establish an unprecedented, 100 % atom‐economic scenario for the catalytic, copper‐mediated monooxygenation of organic substrates, employing both O‐atoms of O 2 .

Topics & Concepts

ChemistryCatalysisCopperBond cleavageExergonic reactionHomolysisDissociation (chemistry)PhotochemistryMedicinal chemistryCrystallographyPhysical chemistryRadicalOrganic chemistryMetal-Catalyzed Oxygenation MechanismsOxidative Organic Chemistry ReactionsMetal complexes synthesis and properties
Catalytic Oxygenation of Hydrocarbons by Mono‐μ‐oxo Dicopper(II) Species Resulting from O−O Cleavage of Tetranuclear Cu <sup>I</sup> /Cu <sup>II</sup> Peroxo Complexes | Litcius