Das, Somnath and Natarajan, Palani and Koenig, Burkhard (2017) Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C-H Amination of Arenes with Carbamates, Urea, and N-Heterocycles. CHEMISTRY-A EUROPEAN JOURNAL, 23 (72). pp. 18161-18165. ISSN 0947-6539, 1521-3765
Full text not available from this repository. (Request a copy)Abstract
The C-H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH(2) as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | LATE-STAGE FUNCTIONALIZATION; CROSS-COUPLING REACTIONS; ORGANIC PHOTOREDOX CATALYSIS; MEDICINAL CHEMISTS TOOLBOX; CHARGE-TRANSFER COMPLEXES; ELECTRON-TRANSFER; EXCITED-STATE; DRUG DESIGN; LIGHT; BENZENE; C-H amination; charge-transfer complexes; electron-deficient arenes; heterocycles; photocatalysis |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 14 Dec 2018 13:18 |
| Last Modified: | 11 Feb 2019 14:45 |
| URI: | https://pred.uni-regensburg.de/id/eprint/1671 |
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