ArticleJournal of the American Chemical Society2023
Electron-Transfer-Enabled Concerted Nucleophilic Fluorination of Azaarenes: Selective C-H Fluorination of Quinolines.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Net fluorine atom transfer from the perspective of a PCET chemist.Chemical communications (Cambridge, England) · 2026Review
- Emerging Strategies forJACS Au · 2026Review
- Ligand-enabled palladium-catalyzed late-stage C-H fluorination of arenes.Chemical science · 2026Article
- Trifluoromethylation of pyridines through skeletal rearrangement.Chemical science · 2026Article
- C3 Selective chalcogenation and fluorination of pyridine using classic Zincke imine intermediates.Nature communications · 2024Article
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Authors and funding
5 authors.
Funding
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Abstract
Direct C-H fluorination is an efficient strategy to construct aromatic C-F bonds, but the cleavage of specific C-H bonds in the presence of other functional groups and the high barrier of C-F bond formation make the transformation challenging. Progress for the electrophilic fluorination of arenes has been reported, but a similar transformation for electron-deficient azaarenes has remained elusive due to the high energy of the corresponding Wheland intermediates. Nucleophilic fluorination of electron-deficient azaarenes is difficult owing to the identity of the Meisenheimer intermediate after fluoride attack, from which fluoride elimination to regenerate the substrate is favored over hydride elimination to form the product. Herein, we report a new concept for C-H nucleophilic fluorination without the formation of azaarene Meisenheimer intermediates through a chain process with an asynchronous concerted F
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