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General and Efficient C–C Bond Forming Photoredox Catalysis with Semiconductor Quantum Dots
Open accessAbstract
Photoredox catalysis has become an essential tool in organic synthesis because it enables new routes to important molecules. However, the best available molecular catalysts suffer from high catalyst loadings and rely on precious metals. Here we show that colloidal nanocrystal quantum dots (QDs) can serve as efficient and robust, precious-metal free, photoassisted redox catalysts. A single-sized CdSe quantum dot (3.0 ± 0.2 nm) can replace several different dye catalysts needed for five different photoredox reactions (β-alkylation, β-aminoalkylation, dehalogenation, amine arylation, and decarboxylative radical formation). Even without optimization of the QDs or the reaction conditions, efficiencies rivaling those of the best available metal dyes were obtained.
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Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
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Zhu, X., Lin, Y., San Martin, J., Sun, Y., Zhu, D., & Yan, Y. (2019) · Nature Communications · doi:10.1038/s41467-019-10634-x · Cited by 455
Lead-Halide Perovskites for Photocatalytic α-Alkylation of Aldehydes
Zhu, X., Lin, Y., Sun, Y., Beard, M. C., & Yan, Y. (2019) · Journal of the American Chemical Society · doi:10.1021/jacs.8b08720 · Cited by 361
Heterogeneous Photocatalysis in Organic Synthesis
Gisbertz, S., & Pieber, B. (2020) · ChemPhotoChem · doi:10.1002/cptc.202000014 · Cited by 312
Zhu, C., Yue, H., Jia, J., & Rueping, M. (2021) · Angewandte Chemie International Edition · doi:10.1002/anie.202013852 · Cited by 259
Metadata
- Authors
- Caputo, J. A., Frenette, L. C., Zhao, N., Sowers, K. L., Krauss, T. D., & Weix, D. J.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-03-10
- Volume
- 139
- Issue
- 12
- Pages
- 4250-4253
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2594617992
- Cited by
- 227
- References
- 1
- FWCI
- 9.29
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Caputo, J. A., Frenette, L. C., Zhao, N., Sowers, K. L., Krauss, T. D., & Weix, D. J. (2017). General and Efficient C–C Bond Forming Photoredox Catalysis with Semiconductor Quantum Dots. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.6b13379
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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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