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Direct Catalytic Anti-Markovnikov Addition of Carboxylic Acids to Alkenes
Open accessAbstract
A direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes is reported. The catalyst system is comprised of the Fukuzumi acridinium photooxidant (1) and a substoichiometric quantity of a hydrogen-atom donor. Oxidizable olefins, such as styrenes, trisubstituted aliphatic alkenes, and enamides, can be employed along with a variety of carboxylic acids to afford the anti-Markovnikov addition adducts exclusively. A deuterium-labeling experiment lends insight to the potential mechanism.
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Citations
Cited by
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Shaw, M. H., Twilton, J., & MacMillan, D. W. C. (2016) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.6b01449 · Cited by 3,186
Dual Catalysis Strategies in Photochemical Synthesis
Skubi, K. L., Blum, T. R., & Yoon, T. P. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00018 · Cited by 2,686
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A Photochemical Strategy for Lignin Degradation at Room Temperature
Nguyen, J. D., Matsuura, B. S., & Stephenson, C. R. J. (2014) · Journal of the American Chemical Society · doi:10.1021/ja4113462 · Cited by 454
Long-Lived Charge Separation and Applications in Artificial Photosynthesis
Fukuzumi, S., Ohkubo, K., & Suenobu, T. (2014) · Accounts of Chemical Research · doi:10.1021/ar400200u · Cited by 411
Romero, N. A., & Nicewicz, D. A. (2014) · Journal of the American Chemical Society · doi:10.1021/ja506228u · Cited by 377
Self-citationMatsui, J. K., Primer, D. N., & Molander, G. A. (2017) · Chemical Science · doi:10.1039/c7sc00283a · Cited by 284
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Metadata
- Authors
- Perkowski, A. J., & Nicewicz, D. A.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-07-03
- Volume
- 135
- Issue
- 28
- Pages
- 10334-10337
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2028208613
- Cited by
- 215
- References
- 0
- FWCI
- 9.94
- Type
- journal article
- Language
- en
- Open access
- green
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