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Catalytic Ketyl-Olefin Cyclizations Enabled by Proton-Coupled Electron Transfer
Abstract
Concerted proton-coupled electron transfer is a key mechanism of substrate activation in biological redox catalysis. However, its applications in organic synthesis remain largely unexplored. Herein, we report the development of a new catalytic protocol for ketyl-olefin coupling and present evidence to support concerted proton-coupled electron transfer being the operative mechanism of ketyl formation. Notably, reaction outcomes were correctly predicted by a simple thermodynamic formalism relating the oxidation potentials and pKa values of specific Brønsted acid/reductant combinations to their capacity to act jointly as a formal hydrogen atom donor.
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Stubbe, J., Nocera, D. G., Yee, C. S., & Chang, M. C. Y. (2003) · Chemical Reviews · doi:10.1021/cr020421u · Cited by 823
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Gentry, E. C., & Knowles, R. R. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00272 · Cited by 773
Self-citationProton-Coupled Electron Transfer Guidelines, Fair and Square
Tyburski, R., Liu, T., Glover, S. D., & Hammarström, L. (2021) · Journal of the American Chemical Society · doi:10.1021/jacs.0c09106 · Cited by 710
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Barham, J. P., & König, B. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.201913767 · Cited by 448
Photochemical Stereocontrol Using Tandem Photoredox–Chiral Lewis Acid Catalysis
Yoon, T. P. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00280 · Cited by 369
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Metadata
- Authors
- Tarantino, K. T., Liu, P., & Knowles, R. R.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-06-28
- Volume
- 135
- Issue
- 27
- Pages
- 10022-10025
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2063790095
- Cited by
- 342
- References
- 1
- FWCI
- 11.30
- Type
- journal article
- Language
- en
- Open access
- closed
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