| Download ( PDF | 946kB) |
Photocarboxylation of Benzylic C-H bonds
Article
Meng, Qing-Yuan
, Schirmer, Tobias, Berger, Anna Lucia, Donabauer, Karsten and König, Burkhard
(2019)
Photocarboxylation of Benzylic C-H bonds.
Journal of the American Chemical Society 141, pp. 11393-11397.
DOI to cite this document: 10.5283/epub.40471
Abstract
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 ...
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.
Alternative links to fulltext
Involved Institutions
Details
| Item type | Article | ||||
| Journal or Publication Title | Journal of the American Chemical Society | ||||
| Publisher | AMER CHEMICAL SOC | ||||
| Place of Publication | WASHINGTON | ||||
| Volume | 141 | ||||
| Page Range | pp. 11393-11397 | ||||
| Date | 2019 | ||||
| Date of publication | 09 Jul 2019 08:59 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König | ||||
| Identification Number |
| ||||
| Keywords | CARBON-DIOXIDE; VISIBLE-LIGHT; CATALYZED CARBOXYLATION; REDUCTION POTENTIALS; ALKENES; CO2; CARBONYLATION; RADICALS; HALIDES; SYSTEM; | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Yes | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-404717 | ||||
| Item ID | 40471 |
Download Statistics
Download Statistics