Majek, Michal and Jacobi von Wangelin, Axel (2015) Metal-Free Carbonylations by Photoredox Catalysis. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 54 (7). pp. 2270-2274. ISSN 1433-7851, 1521-3773
Full text not available from this repository. (Request a copy)Abstract
The synthesis of benzoates from aryl electrophiles and carbon monoxide is a prime example of a transition-metal-catalyzed carbonylation reaction which is widely applied in research and industrial processes. Such reactions proceed in the presence of Pd or Ni catalysts, suitable ligands, and stoichiometric bases. We have developed an alternative procedure that is free of any metal, ligand, and base. The method involves a redox reaction driven by visible light and catalyzed by eosin Y which affords alkyl benzoates from arene diazonium salts, carbon monoxide, and alcohols under mild conditions. Tertiary esters can also be prepared in high yields. DFT calculations and radical trapping experiments support a catalytic photoredox pathway without the requirement for sacrificial redox partners.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ARYL DIAZONIUM SALTS; C-H ARYLATION; VISIBLE-LIGHT; EOSIN-Y; ORGANIC-SYNTHESIS; REDOX POTENTIALS; RADICALS; DYES; DERIVATIVES; COMPLEXES; carbonylation; esters; organocatalysis; photoredox catalysis; redox reaction; visible light |
| Subjects: | 600 Technology > 610 Medical sciences Medicine |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Axel Jacobi von Wangelin |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 24 Jul 2019 11:34 |
| Last Modified: | 24 Jul 2019 11:34 |
| URI: | https://pred.uni-regensburg.de/id/eprint/5968 |
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