Bardagi, Javier I. and Ghosh, Indrajit and Schmalzbauer, Matthias and Ghosh, Tamal and Koenig, Burkhard (2018) Anthraquinones as Photoredox Catalysts for the Reductive Activation of Aryl Halides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (1). pp. 34-40. ISSN 1434-193X, 1099-0690
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Quinones are ubiquitous in nature as structural motifs in natural products and redox mediators in biological electron-transfer processes. Although their oxidation properties have already been used widely in chemical and photochemical reactions, the applications of quinones in reductive photoredox catalysis are less explored. We report the visible-light photoreduction of aryl halides (Ar-X; X = Cl, Br, I) by 1,8-dihydroxyanthraquinone. The resulting aryl radical anions fragment into halide anions and aryl radicals, which react through hydrogen abstraction or C-C bond-forming reactions. The active photocatalyst is generated from 1,8-dihydroxyanthraquinone by photoinduced single-electron reduction to the radical anion or subsequent protonation and further reduction (or vice versa) to the semiquinone anion. Subsequent visible-light excitation of the anthraquinone radical anion or semiquinone anion converts them into very potent single-electron donors. A plausible mechanism for the reaction is proposed on the basis of control experiments and spectroscopic investigations.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | VISIBLE-LIGHT; ELECTRON-TRANSFER; ANION-RADICALS; ARYLATION REACTIONS; ORGANIC-SYNTHESIS; PHOTOCATALYSIS; HETEROARENES; ARENES; BOND; ORGANOCATALYSIS; Photoredox catalysis; Photochemistry; Quinones; Radical ions; Electron transfer; C-H arylation |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 19 Mar 2020 13:09 |
| Last Modified: | 19 Mar 2020 13:09 |
| URI: | https://pred.uni-regensburg.de/id/eprint/15204 |
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