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Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group
Abstract
The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the β-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.
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Cites
Cancer chemopreventive activity of resveratrol, a natural product derived from grapes
Jang, M., Cai, L., Udeani, G. O., Slowing, K. V., Thomas, C. F., Beecher, C. W. W., Fong, H. H. S., Farnsworth, N. R., Kinghorn, A. D., Mehta, R. G., et al. (1997) · Science · doi:10.1126/science.275.5297.218 · Cited by 4,935
Cited by
Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization
Arockiam, P. B., Bruneau, C., & Dixneuf, P. H. (2012) · Chemical Reviews · doi:10.1021/cr300153j · Cited by 2,743
C–C, C–O and C–N bond formation via rhodium(iii)-catalyzed oxidative C–H activation
Song, G., Wang, F., & Li, X. (2012) · Chemical Society Reviews · doi:10.1039/c2cs15281a · Cited by 2,302
Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups
Chen, Z., Wang, B., Zhang, J., Yu, W., Liu, Z., & Zhang, Y. (2015) · Organic Chemistry Frontiers · doi:10.1039/c5qo00004a · Cited by 1,533
Metadata
- Authors
- Mochida, S., Hirano, K., Satoh, T., & Miura, M.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-04-01
- Volume
- 76
- Issue
- 9
- Pages
- 3024-3033
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2334123592
- Cited by
- 235
- References
- 1
- FWCI
- 16.16
- Type
- journal article
- Language
- en
- Open access
- closed
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- Mochida, S., Hirano, K., Satoh, T., & Miura, M. (2011). Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group. The Journal of Organic Chemistry. https://doi.org/10.1021/jo200509m
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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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