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Practical Ni-Catalyzed Aryl–Alkyl Cross-Coupling of Secondary Redox-Active Esters
Open accessAbstract
A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2·6H2O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.
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Citations
Cited by
Modular, stereocontrolled C β –H/C α –C activation of alkyl carboxylic acids
Shang, M., Feu, K. S., Vantourout, J. C., Barton, L. M., Osswald, H. L., Kato, N., Gagaring, K., McNamara, C. W., Chen, G., Hu, L., et al. (2019) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1903048116 · Cited by 53
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Metadata
- Authors
- Cornella, J., Edwards, J. T., Qin, T., Kawamura, S., Wang, J., Pan, C.-M., Gianatassio, R., Schmidt, M., Eastgate, M. D., & Baran, P. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-02-09
- Volume
- 138
- Issue
- 7
- Pages
- 2174-2177
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2261087384
- Cited by
- 449
- References
- 0
- FWCI
- 30.89
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- CoChat. (2026). Citation check: Practical Ni-Catalyzed Aryl–Alkyl Cross-Coupling of Secondary Redox-Active Esters. https://app.cochat.ai/papers/10.1021/jacs.6b00250
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- Cornella, J., Edwards, J. T., Qin, T., Kawamura, S., Wang, J., Pan, C.-M., Gianatassio, R., Schmidt, M., Eastgate, M. D., & Baran, P. S. (2016). Practical Ni-Catalyzed Aryl–Alkyl Cross-Coupling of Secondary Redox-Active Esters. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.6b00250
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