Schmalzbauer, Matthias and Svejstrup, Thomas D. and Fricke, Florian and Brandt, Peter and Johansson, Magnus J. and Bergonzini, Giulia and Koenig, Burkhard (2020) Redox-Neutral Photocatalytic C-H Carboxylation of Arenes and Styrenes with CO2. CHEM, 6 (10). pp. 2658-2672. ISSN 2451-9294,
Full text not available from this repository. (Request a copy)Abstract
Carbon dioxide (CO2) is an attractive one-carbon (C1) building block in terms of sustainability and abundance. However, its low reactivity limits applications in organic synthesis as typically high-energy reagents are required to drive transformations. Here, we present a redox-neutral C-H carboxylation of arenes and styrenes using a photocatalytic approach. Upon blue-light excitation, the anthrolate anion photocatalyst is able to reduce many aromatic compounds to their corresponding radical anions, which react with CO2 to afford carboxylic acids. High-throughput screening and computational analysis suggest that a correct balance between electron affinity and nucleophilicity of substrates is essential. This novel methodology enables the carboxylation of numerous aromatic compounds, including many that are not tolerated in classical carboxylation chemistry. Over 50 examples of C-H functionalizations using CO2 or ketones illustrate a broad applicability. The method opens new opportunities for the valorization of common arenes and may find application in late-stage C-H carboxylation.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CATALYZED DIRECT CARBOXYLATION; ACID-MEDIATED CARBOXYLATION; CARBON-DIOXIDE; VISIBLE-LIGHT; REDUCTIVE CARBOXYLATION; AROMATIC-COMPOUNDS; BONDS; HYDROCARBOXYLATION; BETA; PALLADIUM; |
| 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: | 09 Mar 2021 07:25 |
| Last Modified: | 09 Mar 2021 07:25 |
| URI: | https://pred.uni-regensburg.de/id/eprint/43587 |
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