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- W4385667048 abstract "Over the past decade, numerous reports have focused on the development and applications of Cu-mediated C–H functionalization reactions; however, to date, little is known about the Cu intermediates involved in these transformations. This paper details the observation and characterization of CuII and CuIII intermediates in aminoquinoline-directed C(sp2)–H functionalization of a fluoroarene substrate. An initial C(sp2)–H activation at CuII occurs at room temperature to afford an isolable anionic cyclometalated CuII complex. This complex undergoes single-electron oxidation with ferrocenium or AgI salts under mild conditions (5 min at room temperature) to afford C(sp2)–C(sp2) or C(sp2)–NO2 coupling products. Spectroscopic studies implicate the formation of a transient diamagnetic CuIII-σ-aryl intermediate that undergoes either (i) a second C(sp2)–H activation at CuIII followed by C–C bond-forming reductive elimination or (ii) reaction with a NO2– nucleophile and C(sp2)–NO2 coupling." @default.
- W4385667048 created "2023-08-09" @default.
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- W4385667048 date "2023-08-08" @default.
- W4385667048 modified "2023-10-17" @default.
- W4385667048 title "Characterization and Reactivity of Copper(II) and Copper(III) σ-Aryl Intermediates in Aminoquinoline-Directed C–H Functionalization" @default.
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- W4385667048 doi "https://doi.org/10.1021/jacs.3c00914" @default.
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