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Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans
Open accessAbstract
High Resolution Image Download MS PowerPoint Slide The 2,3-dihydrobenzofuran scaffold is widely found in natural products and biologically active compounds. Herein, dearomatizing 2,3-fluoroaroylation of benzofurans with aroyl fluorides as bifunctional reagents to access 2,3-difunctionalized dihydrobenzofurans is reported. The reaction that occurs by cooperative NHC/photoredox catalysis provides 3-aroyl-2-fluoro-2,3-dihydrobenzofurans with moderate to good yield and high diastereoselectivity. Cascades proceed via radical/radical cross-coupling of a benzofuran radical cation generated in the photoredox catalysis cycle with a neutral ketyl radical formed through the NHC catalysis cycle. The redox-neutral transformation exhibits broad substrate scope and high functional group compatibility. With anhydrides as bifunctional reagents, dearomatizing aroyloxyacylation of benzofurans is achieved and the strategy can also be applied to N -acylated indoles to afford 3-aroyl-2-fluoro-dihydroindoles.
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Cites
Prier, C. K., Rankic, D. A., & MacMillan, D. W. C. (2013) · Chemical Reviews · doi:10.1021/cr300503r · Cited by 9,590
Cited by
Liu, K., Schwenzer, M., & Studer, A. (2022) · ACS Catalysis · doi:10.1021/acscatal.2c03996 · Cited by 325
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Metadata
- Authors
- Yu, X., Meng, Q.-Y., Daniliuc, C. G., & Studer, A.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2022-03-22
- Volume
- 144
- Issue
- 16
- Pages
- 7072-7079
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W4221001123
- Cited by
- 163
- References
- 1
- FWCI
- 12.98
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Yu, X., Meng, Q.-Y., Daniliuc, C. G., & Studer, A. (2022). Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans. Journal of the American Chemical Society. https://doi.org/10.1021/jacs.2c01735
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