Meng, Qing-Yuan and Schirmer, Tobias E. and Berger, Anna Lucia and Donabauer, Karsten and Koenig, Burkhard (2019) Photocarboxylation of Benzylic C-H Bonds. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 141 (29). pp. 11393-11397. ISSN 0002-7863, 1520-5126
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The carboxylation of sp(3)-hybridized C-H bonds with CO2 is a challenging transformation. Herein, we report a visible-light-mediated carboxylation of benzylic C-H bonds with CO2 into 2-arylpropionic acids under metal-free conditions. Photo-oxidized triisopropylsilanethiol was used as the hydrogen atom transfer catalyst to afford a benzylic radical that accepts an electron from the reduced form of 2,3,4,6-tetra(9H-carbazol-9-yl)-5-(1-phenylethyl)benzonitrile generated in situ. The resulting benzylic carbanion reacts with CO2 to generate the corresponding carboxylic acid after protonation. The reaction proceeded without the addition of any sacrificial electron donor, electron acceptor or stoichiometric additives. Moderate to good yields of the desired products were obtained in a broad substrate scope. Several drugs were successfully synthesized using the novel strategy.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CARBON-DIOXIDE; VISIBLE-LIGHT; CATALYZED CARBOXYLATION; REDUCTION POTENTIALS; ALKENES; CO2; CARBONYLATION; RADICALS; HALIDES; SYSTEM; |
| 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: | 02 Apr 2020 11:17 |
| Last Modified: | 02 Apr 2020 11:17 |
| URI: | https://pred.uni-regensburg.de/id/eprint/26608 |
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