The DOI matches its Crossref record; 42 of the 42 references it cites were found in a registry or an index.
Photocarboxylation of Benzylic C–H Bonds
Open accessAbstract
Abstract The carboxylation of sp3-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.
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Cites
Highly efficient organic light-emitting diodes from delayed fluorescence
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Using carbon dioxide as a building block in organic synthesis
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Simmons, E. M., & Hartwig, J. F. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201107334 · Cited by 2,136
Hydrocarbon Bond Dissociation Energies
McMillen, D. F., & Golden, D. M. (1982) · Annual Review of Physical Chemistry · doi:10.1146/annurev.pc.33.100182.002425 · Cited by 2,005
The synthesis of organic carbonates from carbon dioxide
Sakakura, T., & Kohno, K. (2009) · Chemical Communications · doi:10.1039/b819997c · Cited by 1,067
Transition-metal-catalyzed C–C bond formation through the fixation of carbon dioxide
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Transition‐Metal‐Catalyzed Carboxylation Reactions with Carbon Dioxide
Tortajada, A., Juliá‐Hernández, F., Börjesson, M., Moragas, T., & Martin, R. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201803186 · Cited by 706
Cited by
Photoredox-Catalyzed C–H Functionalization Reactions
Holmberg-Douglas, N., & Nicewicz, D. A. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00311 · Cited by 989
Photocatalytic Late-Stage C–H Functionalization
Bellotti, P., Huang, H.-M., Faber, T., & Glorius, F. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00478 · Cited by 623
Visible-Light-Driven Reductive Carboarylation of Styrenes with CO 2 and Aryl Halides
Wang, H., Gao, Y., Zhou, C., & Li, G. (2020) · Journal of the American Chemical Society · doi:10.1021/jacs.0c03144 · Cited by 303
Metadata
- Authors
- Meng, Q.-Y., Schirmer, T. E., Berger, A. L., Donabauer, K., & König, B.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-07-08
- Volume
- 141
- Issue
- 29
- Pages
- 11393-11397
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2959967536
- Cited by
- 313
- References
- 42
- FWCI
- 14.75
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Meng, Q.-Y., Schirmer, T. E., Berger, A. L., Donabauer, K., & König, B. (2019). Photocarboxylation of Benzylic C–H Bonds. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.9b05360
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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