Triflyl [ 18 F]Fluoride as a Solution for Base‐Sensitive Late‐Stage Nucleophilic Aromatic 18 F‐Fluorination Reactions
Fluorine‐18 is the predominant radionuclide used to label Positron Emission Tomography (PET) tracers. One outstanding challenge in nucleophilic aromatic radiofluorination reactions is the sensitivity of precursors and catalysts for basic reaction conditions, which are necessary for the work‐up of [...
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| Published in | Chemistry : a European journal Vol. 31; no. 2; p. e202403127 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
09.01.2025
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0947-6539 1521-3765 |
| DOI | 10.1002/chem.202403127 |
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| Abstract | Fluorine‐18 is the predominant radionuclide used to label Positron Emission Tomography (PET) tracers. One outstanding challenge in nucleophilic aromatic radiofluorination reactions is the sensitivity of precursors and catalysts for basic reaction conditions, which are necessary for the work‐up of [
18
F]fluoride, resulting in limited reproducibility. Triflyl [
18
F]fluoride is a new [
18
F]fluoride source that allows freedom in choice of type and amounts of base and cryptand. The aim of the current work is to explore the scope and limitations of triflyl [
18
F]fluoride in the late‐stage nucleophilic aromatic
18
F‐fluorination of various functionalized precursors, exploring reduced amounts of base and cryptand. The assessment allowed for the application of this new nucleophilic [
18
F]fluoride reagent to the successful radiosynthesis of boron, stannane, hypervalent iodonium ylide and phenol substrates bearing electron‐deficient, ‐neutral and ‐rich functional groups as well as the clinically relevant PET tracers [
18
F]FPEB, [
18
F]
m
FBG and [
18
F]SynVesT‐1. |
|---|---|
| AbstractList | Fluorine‐18 is the predominant radionuclide used to label Positron Emission Tomography (PET) tracers. One outstanding challenge in nucleophilic aromatic radiofluorination reactions is the sensitivity of precursors and catalysts for basic reaction conditions, which are necessary for the work‐up of [
18
F]fluoride, resulting in limited reproducibility. Triflyl [
18
F]fluoride is a new [
18
F]fluoride source that allows freedom in choice of type and amounts of base and cryptand. The aim of the current work is to explore the scope and limitations of triflyl [
18
F]fluoride in the late‐stage nucleophilic aromatic
18
F‐fluorination of various functionalized precursors, exploring reduced amounts of base and cryptand. The assessment allowed for the application of this new nucleophilic [
18
F]fluoride reagent to the successful radiosynthesis of boron, stannane, hypervalent iodonium ylide and phenol substrates bearing electron‐deficient, ‐neutral and ‐rich functional groups as well as the clinically relevant PET tracers [
18
F]FPEB, [
18
F]
m
FBG and [
18
F]SynVesT‐1. Fluorine-18 is the predominant radionuclide used to label Positron Emission Tomography (PET) tracers. One outstanding challenge in nucleophilic aromatic radiofluorination reactions is the sensitivity of precursors and catalysts for basic reaction conditions, which are necessary for the work-up of [ F]fluoride, resulting in limited reproducibility. Triflyl [ F]fluoride is a new [ F]fluoride source that allows freedom in choice of type and amounts of base and cryptand. The aim of the current work is to explore the scope and limitations of triflyl [ F]fluoride in the late-stage nucleophilic aromatic F-fluorination of various functionalized precursors, exploring reduced amounts of base and cryptand. The assessment allowed for the application of this new nucleophilic [ F]fluoride reagent to the successful radiosynthesis of boron, stannane, hypervalent iodonium ylide and phenol substrates bearing electron-deficient, -neutral and -rich functional groups as well as the clinically relevant PET tracers [ F]FPEB, [ F]mFBG and [ F]SynVesT-1. |
| Author | de Kruijff, Anna M. T. Windhorst, Albert D. Vugts, Danielle J. Haveman, Lizeth Y. F. van Eeden, Sjoerd P. P. |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/39530382$$D View this record in MEDLINE/PubMed |
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| Keywords | Triflyl [18F]fluoride Fluorine-18 Positron emission tomography Radiochemistry |
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| Snippet | Fluorine‐18 is the predominant radionuclide used to label Positron Emission Tomography (PET) tracers. One outstanding challenge in nucleophilic aromatic... Fluorine-18 is the predominant radionuclide used to label Positron Emission Tomography (PET) tracers. One outstanding challenge in nucleophilic aromatic... |
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| Title | Triflyl [ 18 F]Fluoride as a Solution for Base‐Sensitive Late‐Stage Nucleophilic Aromatic 18 F‐Fluorination Reactions |
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