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Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans

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Yu, Xiaoye, Meng, Qing-Yuan, Daniliuc, Constantin G., Studer, Armido·2022·Journal of the American Chemical Society

Abstract

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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Metadata

Authors
Yu, X., Meng, Q.-Y., Daniliuc, C. G., & Studer, A.
Venue
Journal of the American Chemical Society
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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CoChat. (2026). Citation check: Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans. https://app.cochat.ai/papers/10.1021/jacs.2c01735
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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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