Schmalzbauer, Matthias and Ghosh, Indrajit and Koenig, Burkhard (2019) Utilising excited state organic anions for photoredox catalysis: activation of (hetero)aryl chlorides by visible light-absorbing 9-anthrolate anions. FARADAY DISCUSSIONS, 215. pp. 364-378. ISSN 1359-6640, 1364-5498
Full text not available from this repository. (Request a copy)Abstract
The tricyclic aromatic ketone 9-anthrone and its derivatives are under basic conditions in equilibrium with their corresponding anionic forms. Unlike the neutral species, the 9-anthrolate anions can be excited by blue LED light and thus, are able to initiate a photoinduced electron transfer (PET) reaction. To demonstrate the synthetic applicability of the catalytic system, various (hetero)aryl chlorides were converted in C-C and C-Het bond-forming reactions affording the corresponding arylation products in moderate to excellent yields. The reactions proceed under very mild conditions without the need for a sacrificial electron donor. Besides 9-anthrone, other closely related derivatives were synthesised and investigated concerning their ability to catalyse demanding reductive transformations. Based on spectroscopic findings and radical trapping experiments a conceivable mechanism is proposed.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ELECTRON-TRANSFER; METAL-FREE; RADICALS; BOND; HETEROARENES; GENERATION; ARYLATION; PHENOLS; |
| 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: | 03 Apr 2020 11:48 |
| Last Modified: | 03 Apr 2020 11:48 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26717 |
Actions (login required)
 |
View Item |
