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Efficient Visible Light Photocatalysis of [2+2] Enone Cycloadditions
Abstract
We report that Ru(bipy)3Cl2 can serve as a visible light photocatalyst for [2+2] enone cycloadditions. A variety of aryl enones participate readily in the reaction, and the diastereoselectivity in the formation of the cyclobutane products is excellent. We propose a mechanism in which a photogenerated Ru(bipy)3+ complex promotes one-electron reduction of the enone substrate, which undergoes subsequent radical anion cycloaddition. The efficiency of this process is extremely high, which allows rapid, high-yielding [2+2] cyclizations to be conducted using incident sunlight as the only source of irradiation.
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Citations
Cited by
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Visible light photocatalysis as a greener approach to photochemical synthesis
Yoon, T. P., Ischay, M. A., & Du, J. (2010) · Nature Chemistry · doi:10.1038/nchem.687 · Cited by 2,657
Self-citationPhotoredox Catalysis with Visible Light
Zeitler, K. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200904056 · Cited by 991
Control of a Living Radical Polymerization of Methacrylates by Light
Fors, B. P., & Hawker, C. J. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201203639 · Cited by 820
Tay, N. E. S., Lehnherr, D., & Rovis, T. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00384 · Cited by 518
Metadata
- Authors
- Ischay, M. A., Anzovino, M. E., Du, J., & Yoon, T. P.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-09-04
- Volume
- 130
- Issue
- 39
- Pages
- 12886-12887
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1999601844
- Cited by
- 1,167
- References
- 0
- FWCI
- 16.84
- Type
- journal article
- Language
- en
- Open access
- closed
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- Ischay, M. A., Anzovino, M. E., Du, J., & Yoon, T. P. (2008). Efficient Visible Light Photocatalysis of [2+2] Enone Cycloadditions. Journal of the American Chemical Society. https://doi.org/10.1021/ja805387f
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