ArticleNature chemistry2019
α-Fluorination of carbonyls with nucleophilic fluorine.
Article in Nature chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
28 citing papers in PubMed.
- Electrochemical Synthesis of Isolated Fluoride Reagents from PFAS.Journal of the American Chemical Society · 2026Article
- Origami with small molecules: exploiting the C-F bond as a conformational tool.Beilstein journal of organic chemistry · 2025Review
- Asymmetric Synthesis of β-Ketoamides by Sulfonium Rearrangement.Angewandte Chemie (International ed. in English) · 2024Article
- Article
- Speciation and kinetics of fluoride transfer from tetra-Chemical science · 2024Article
- Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas.Beilstein journal of organic chemistry · 2024Article
- Simple and Efficient Aromatic C-H Oxazolination.Precision chemistry · 2023Article
- New Strategies for the Functionalization of Carbonyl Derivatives via α-Umpolung: From Enolates to Enolonium Ions.Accounts of chemical research · 2023Article
- Design, synthesis, crystal structure, and in vitro antibacterial activities of sulfonamide derivatives bearing the 4-aminoquinazoline moiety.Molecular diversity · 2023Article
- Regiodivergent Nucleophilic Fluorination under Hydrogen Bonding Catalysis: A Computational and Experimental Study.Journal of the American Chemical Society · 2023Article
- BenchtopACS omega · 2023Article
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (International ed. in English) · 2022Review
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Review
- α-Thianthrenium Carbonyl Species: The Equivalent of an α-Carbonyl Carbocation.Angewandte Chemie (International ed. in English) · 2022Article
- One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines.Molecules (Basel, Switzerland) · 2022Article
- Sulfur(iv)-mediated umpolung α-heterofunctionalization of 2-oxazolines.Chemical science · 2022Article
- Enzymatic synthesis of fluorinated compounds.Applied microbiology and biotechnology · 2021Review
- Uniting Amide Synthesis and Activation by PJournal of the American Chemical Society · 2021Article
- Chemoselektive γ-Oxidation von β,γ-ungesättigten Amiden mit TEMPO.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Given the unique properties of fluorine, and the ability of fluorination to change the properties of organic molecules, there is significant interest from medicinal chemists in innovative methodologies that enable the synthesis of new fluorinated motifs. State-of-the-art syntheses of α-fluorinated carbonyl compounds invariably rely on electrophilic fluorinating agents, which can be strongly oxidizing and difficult to handle. Here we show that reversing the polarity of the enolate partner to that of an enolonium enables nucleophilic fluorinating agents to be used for direct chemoselective α-C-H-fluorination of amides. Reduction of these products enables facile access to β-fluorinated amines and the value of this methodology is shown by the easy preparation of a number of fluorinated analogues of drugs and agrochemicals. A fluorinated analogue of citalopram, a marketed antidepressant drug, is presented as an example of the preserved biological activity after fluorination.
Indexed as
Identifiers
30833720What OpenQuestion holds
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.