Chatterjee, Anamitra and Koenig, Burkhard (2019) Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 58 (40). pp. 14289-14294. ISSN 1433-7851, 1521-3773
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The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SODIUM-BOROHYDRIDE; VISIBLE-LIGHT; UP-CONVERSION; REDUCTION; CATALYSIS; ANTHRACENE; WATER; dearomatization; electron transfer; energy transfer; photocatalysis; reduction |
| 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: | 31 Mar 2020 09:25 |
| Last Modified: | 31 Mar 2020 09:25 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26400 |
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