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Modulating Reactivity and Diverting Selectivity in Palladium-Catalyzed Heteroaromatic Direct Arylation Through the Use of a Chloride Activating/Blocking Group
Abstract
Through the introduction of an aryl chloride substituent, the selectivity of palladium-catalyzed direct arylation may be diverted to provide alternative regioisomeric products in high yields. In cases where low reactivity is typically observed, the presence of the carbon-chlorine bond can serve to enhance reactivity and provide superior outcomes. From a strategic perspective, the C-Cl bond is easily introduced and can be employed in a variety of subsequent transformations to provide a wealth of highly functionalized heterocycles with minimal substrate preactivation. The impact of the C-Cl functional group on direct arylation reactivity has also been evaluated mechanistically, and the observed reactivity profiles correlate very well with that predicted by a concerted metalation-deprotonation pathway.
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Cites
Density-functional thermochemistry. III. The role of exact exchange
Becke, A. D. (1993) · The Journal of Chemical Physics · doi:10.1063/1.464913 · Cited by 103,767
Lee, C., Yang, W., & Parr, R. G. (1988) · Physical Review B · doi:10.1103/physrevb.37.785 · Cited by 100,874
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Davies, D. L., Macgregor, S. A., & McMullin, C. L. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00839 · Cited by 585
Gorelsky, S. I., Lapointe, D., & Fagnou, K. (2012) · The Journal of Organic Chemistry · doi:10.1021/jo202342q · Cited by 438
Self-citationRousseaux, S., Gorelsky, S. I., Chung, B. K. W., & Fagnou, K. (2010) · Journal of the American Chemical Society · doi:10.1021/ja103081n · Cited by 278
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Metadata
- Authors
- Liégault, B., Petrov, I., Gorelsky, S. I., & Fagnou, K.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-01-14
- Volume
- 75
- Issue
- 4
- Pages
- 1047-1060
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W1992766570
- Cited by
- 316
- References
- 2
- FWCI
- 19.26
- Type
- journal article
- Language
- en
- Open access
- closed
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- Liégault, B., Petrov, I., Gorelsky, S. I., & Fagnou, K. (2010). Modulating Reactivity and Diverting Selectivity in Palladium-Catalyzed Heteroaromatic Direct Arylation Through the Use of a Chloride Activating/Blocking Group. The Journal of Organic Chemistry. https://doi.org/10.1021/jo902515z
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