ArticleNature2016
Concerted nucleophilic aromatic substitution with (19)F(-) and (18)F(-).
Article in Nature, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 45 papers.
What it found
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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
45 citing papers in PubMed, 280 citations in OpenAlex.
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- Exceptions, Paradoxes, and Their Resolutions in Chemical Reactivity.The Journal of organic chemistry · 2024Review
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- Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Deoxyfluorination of phenols for chemoselectiveNature protocols · 2023Review
- State of the art procedures towards reactive [EJNMMI radiopharmacy and chemistry · 2023Review
- A broadly applicable quantitative relative reactivity model for nucleophilic aromatic substitution (SChemical science · 2022Article
- Mechanistic Investigations into Amination of Unactivated Arenes via Cation Radical Accelerated Nucleophilic Aromatic Substitution.Journal of the American Chemical Society · 2022Article
- Mechanism of Visible Light-Mediated Alkene Aminoarylation with Arylsulfonylacetamides.ACS catalysis · 2022Article
- Kinetics and Reaction Mechanism of Biothiols Involved in SFrontiers in chemistry · 2022Article
- Direct Cu-mediated aromaticChemical science · 2021Article
- Synthesis and biological evaluation of PET tracers designed for imaging of calcium activated potassium channel 3.1 (KRSC advances · 2021Article
- Ultrafast Photoclick Reaction for SelectiveJournal of the American Chemical Society · 2021Article
- Triarylmethanes and their Medium-Ring Analogues by Unactivated Truce-Smiles Rearrangement of Benzanilides.Angewandte Chemie (International ed. in English) · 2021Article
- Trialkylammonium salt degradation: implications for methylation and cross-coupling.Chemical science · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
Abstract
Nucleophilic aromatic substitution (SNAr) is widely used by organic chemists to functionalize aromatic molecules, and it is the most commonly used method to generate arenes that contain (18)F for use in positron-emission tomography (PET) imaging. A wide range of nucleophiles exhibit SNAr reactivity, and the operational simplicity of the reaction means that the transformation can be conducted reliably and on large scales. During SNAr, attack of a nucleophile at a carbon atom bearing a 'leaving group' leads to a negatively charged intermediate called a Meisenheimer complex. Only arenes with electron-withdrawing substituents can sufficiently stabilize the resulting build-up of negative charge during Meisenheimer complex formation, limiting the scope of SNAr reactions: the most common SNAr substrates contain strong π-acceptors in the ortho and/or para position(s). Here we present an unusual concerted nucleophilic aromatic substitution reaction (CSNAr) that is not limited to electron-poor arenes, because it does not proceed via a Meisenheimer intermediate. We show a phenol deoxyfluorination reaction for which CSNAr is favoured over a stepwise displacement. Mechanistic insights enabled us to develop a functional-group-tolerant (18)F-deoxyfluorination reaction of phenols, which can be used to synthesize (18)F-PET probes. Selective (18)F introduction, without the need for the common, but cumbersome, azeotropic drying of (18)F, can now be accomplished from phenols as starting materials, and provides access to (18)F-labelled compounds not accessible through conventional chemistry.
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What 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.