Petzold, Daniel and Koenig, Burkhard (2018) Photocatalytic Oxidative Bromination of Electron-Rich Arenes and Heteroarenes by Anthraquinone. ADVANCED SYNTHESIS & CATALYSIS, 360 (4). pp. 626-630. ISSN 1615-4150, 1615-4169
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The estimated excited oxidation potential of sodium anthraquinone-2-sulfonate (SAS) increases from 1.8 V to about 2.3 V vs SCE by protonation with Bronsted acids. This increased photooxidation power of protonated anthraquinone was used for the regio-selective oxidative bromination of electron rich (hetero) arenes and drugs in good yield. The mild reaction conditions are compatible with many functional groups, such as double and triple bonds, ketones, amides and amines, hydroxyl groups, carboxylic acids and carbamates. Mechanistic investigations indicate the photooxidation of the arene followed by nucleophilic bromide addition as the likely pathway.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOREDOX CATALYSIS; FLUORESCENCE; MOLECULES; KINETICS; Photocatalysis; protonation; proton coupled electron transfer; halogenation; oxidation |
| 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: | 18 Mar 2020 09:16 |
| Last Modified: | 18 Mar 2020 09:16 |
| URI: | https://pred.uni-regensburg.de/id/eprint/15041 |
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