ArticleScientific reports2015
Sulfonium salts as leaving groups for aromatic labelling of drug-like small molecules with fluorine-18.
Article in Scientific reports, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed.
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- Oxidation-Cyclisation of Biphenyl Thioethers to Dibenzothiophenium Salts for UltrarapidInternational journal of molecular sciences · 2022Article
- Arene radiofluorination enabled by photoredox-mediated halide interconversion.Nature chemistry · 2022Article
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- Automated Synthesis and Initial Evaluation of (4'-Amino-5',8'-difluoro-1'H-spiro[piperidine-4,2'-quinazolin]-1-yl)(4-[Molecular imaging · 2021Article
- Site-Selective Late-Stage Aromatic [Angewandte Chemie (International ed. in English) · 2020Article
- Synthesis and in vivo evaluation of [European journal of nuclear medicine and molecular imaging · 2019Article
- Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.Chemical reviews · 2019Article
- FacileNature protocols · 2019Article
- Synthesis and in Vivo Evaluation of a Novel PET Radiotracer for Imaging of Synaptic Vesicle Glycoprotein 2A (SV2A) in Nonhuman Primates.ACS chemical neuroscience · 2019Article
- Chemistry for Positron Emission Tomography: Recent Advances inAngewandte Chemie (International ed. in English) · 2019Review
- Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for AromaticJournal of the American Chemical Society · 2018Article
- [ACS omega · 2017Article
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Authors and funding
7 authors.
Funding
Abstract
Positron emission tomography (PET) is unique in that it allows quantification of biochemical processes in vivo, but difficulties with preparing suitably labelled radiotracers limit its scientific and diagnostic applications. Aromatic [(18)F]fluorination of drug-like small molecules is particularly challenging as their functional group compositions often impair the labelling efficiency. Herein, we report a new strategy for incorporation of (18)F into highly functionalized aromatic compounds using sulfonium salts as leaving groups. The method is compatible with pharmacologically relevant functional groups, including aliphatic amines and basic heterocycles. Activated substrates react with [(18)F]fluoride at room temperature, and with heating the reaction proceeds in the presence of hydrogen bond donors. Furthermore, the use of electron rich spectator ligands allows efficient and regioselective [(18)F]fluorination of non-activated aromatic moieties. The method provides a broadly applicable route for (18)F labelling of biologically active small molecules, and offers immediate practical benefits for drug discovery and imaging with PET.
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