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Oxidative C−H Activation/C−C Bond Forming Reactions: Synthetic Scope and Mechanistic Insights
Abstract
This paper describes a new palladium-catalyzed method for C-H activation/carbon-carbon bond formation with hypervalent iodine arylating agents. This transformation has been applied to a variety of arene and benzylic substrates containing different directing groups (pyridines, quinolines, oxazolidinones, and amides) and proceeds with high levels of regiocontrol. Mechanistic experiments provide preliminary evidence in support of an unusual mechanism for this transformation involving a Pd(II)/Pd(IV) catalytic cycle.
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Citations
Cited by
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Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis
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Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups
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Controlling Site Selectivity in Palladium-Catalyzed C–H Bond Functionalization
Neufeldt, S. R., & Sanford, M. S. (2012) · Accounts of Chemical Research · doi:10.1021/ar300014f · Cited by 1,360
Self-citationKalyani, D., McMurtrey, K. B., Neufeldt, S. R., & Sanford, M. S. (2011) · Journal of the American Chemical Society · doi:10.1021/ja208068w · Cited by 676
Self-citationDeprez, N. R., & Sanford, M. S. (2009) · Journal of the American Chemical Society · doi:10.1021/ja904116k · Cited by 522
Self-citationCopper-Catalyzed Arylation and Alkenylation of Polyfluoroarene C−H Bonds
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Visible-light radical reaction designed by Ru- and Ir-based photoredox catalysis
Koike, T., & Akita, M. (2014) · Inorg. Chem. Front. · doi:10.1039/c4qi00053f · Cited by 454
Inamoto, K., Hasegawa, C., Hiroya, K., & Doi, T. (2008) · Organic Letters · doi:10.1021/ol802033p · Cited by 290
Rousseaux, S., Gorelsky, S. I., Chung, B. K. W., & Fagnou, K. (2010) · Journal of the American Chemical Society · doi:10.1021/ja103081n · Cited by 278
Direct Pd-Catalyzed Arylation of 1,2,3-Triazoles
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Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles
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Metadata
- Authors
- Kalyani, D., Deprez, N. R., Desai, L. V., & Sanford, M. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-05-03
- Volume
- 127
- Issue
- 20
- Pages
- 7330-7331
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2071053863
- Cited by
- 796
- References
- 0
- FWCI
- 27.59
- Type
- journal article
- Language
- en
- Open access
- closed
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