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Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed Ortho-Olefination and Decarboxylation of Benzoic Acids
Abstract
Ortho-substituted benzoic acids efficiently undergo precisely ordered ortho-olefination/decarboxylation upon treatment with styrenes in the presence of a rhodium catalyst and silver salt oxidant to afford the corresponding meta-substituted stilbene derivatives. The selective syntheses of 1,3- and 1,4-distyrylbenzenes have also been realized through the reactions of simple benzoic acid and phthalic acid, respectively, with styrene under similar conditions.
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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
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-11-18
- Volume
- 12
- Issue
- 24
- Pages
- 5776-5779
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2312433358
- Cited by
- 207
- References
- 1
- FWCI
- 11.37
- Type
- journal article
- Language
- en
- Open access
- closed
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- Mochida, S., Hirano, K., Satoh, T., & Miura, M. (2010). Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed Ortho-Olefination and Decarboxylation of Benzoic Acids. Organic Letters. https://doi.org/10.1021/ol1027392
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