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Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O₂ Model Systems to Organometallic Transformations

Trammell, Rachel, Rajabimoghadam, Khashayar, Garcia-Bosch, Isaac
Chemical reviews 2019 v.119 no.4 pp. 2954-3031
bioavailability, catalytic activity, copper, enzymes, hydrogen peroxide, models, oxidants, oxygen, palladium, platinum, reaction mechanisms, rhodium, toxicity
Copper is one of the most abundant and less toxic transition metals. Nature takes advantage of the bioavailability and rich redox chemistry of Cu to carry out oxygenase and oxidase organic transformations using O₂ (or H₂O₂) as oxidant. Inspired by the reactivity of these Cu-dependent metalloenzymes, chemists have developed synthetic protocols to functionalize organic molecules under enviormentally benign conditions. Copper also promotes other transformations usually catalyzed by 4d and 5d transition metals (Pd, Pt, Rh, etc.) such as nitrene insertions or C–C and C–heteroatom coupling reactions. In this review, we summarized the most relevant research in which copper promotes or catalyzes the functionalization of organic molecules, including biological catalysis, bioinspired model systems, and organometallic reactivity. The reaction mechanisms by which these processes take place are discussed in detail.