ArticleNature2018
Palladium-catalysed electrophilic aromatic C-H fluorination.
Article in Nature, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed, 169 citations in OpenAlex.
- A unified strategy for remote C-H fluorination of phenylacetic acids and their homologues at theChemical science · 2026Article
- Single-iron catalyst with heterogenized TEMPO for selective toluene electrooxidation to benzaldehyde at low potentials.Nature communications · 2026Article
- Thianthrenium Salts in Photochemistry.Accounts of chemical research · 2026Article
- Ligand-Controlled NondirectedACS catalysis · 2024Article
- (P^N^C) Ligands to Stabilize Gold(III): A Straightforward Access to Hydroxo, Formate, and Hydride Complexes.Inorganic chemistry · 2024Article
- Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing.Acta pharmaceutica Sinica. B · 2024Review
- Electron-Transfer-Enabled Concerted Nucleophilic Fluorination of Azaarenes: Selective C-H Fluorination of Quinolines.Journal of the American Chemical Society · 2023Article
- Dual-Ligand Catalyst for the Nondirected C-H Olefination of Heteroarenes.Journal of the American Chemical Society · 2023Article
- Copper-catalyzed defluorinative arylboration of vinylarenes with polyfluoroarenes.Chemical science · 2023Article
- Copper-Catalyzed Electrochemical C-H Fluorination.Chem catalysis · 2023Article
- A Perspective on Late-Stage Aromatic C-H Bond Functionalization.Journal of the American Chemical Society · 2022Article
- Ring-opening fluorination of bicyclic azaarenes.Chemical science · 2022Article
- Article
- High Site Selectivity in Electrophilic Aromatic Substitutions: Mechanism of C-H Thianthrenation.Journal of the American Chemical Society · 2021Article
- Decarboxylative Polyfluoroarylation of Alkylcarboxylic Acids.Angewandte Chemie (International ed. in English) · 2021Article
- Fluoroarene Separations in Metal-Organic Frameworks with Two Proximal MgJournal of the American Chemical Society · 2021Article
- Direct C(spNature communications · 2020Article
- Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Site-Selective Late-Stage Aromatic [Angewandte Chemie (International ed. in English) · 2020Article
- Where Is the Fluoro Wall?: A Quantum Chemical Investigation.Inorganic chemistry · 2020Article
Corrections and comments
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Authors and funding
11 authors at 3 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Aryl fluorides are widely used in the pharmaceutical and agrochemical industries, and recent advances have enabled their synthesis through the conversion of various functional groups. However, there is a lack of general methods for direct aromatic carbon-hydrogen (C-H) fluorination. Conventional methods require the use of either strong fluorinating reagents, which are often unselective and difficult to handle, such as elemental fluorine, or less reactive reagents that attack only the most activated arenes, which reduces the substrate scope. A method for the direct fluorination of aromatic C-H bonds could facilitate access to fluorinated derivatives of functional molecules that would otherwise be difficult to produce. For example, drug candidates with improved properties, such as increased metabolic stability or better blood-brain-barrier penetration, may become available. Here we describe an approach to catalysis and the resulting development of an undirected, palladium-catalysed method for aromatic C-H fluorination using mild electrophilic fluorinating reagents. The reaction involves a mode of catalysis that is unusual in aromatic C-H functionalization because no organometallic intermediate is formed; instead, a reactive transition-metal-fluoride electrophile is generated catalytically for the fluorination of arenes that do not otherwise react with mild fluorinating reagents. The scope and functional-group tolerance of this reaction could provide access to functional fluorinated molecules in pharmaceutical and agrochemical development that would otherwise not be readily accessible.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.