Synthesis of 18F‑Labeled Aryl Fluorosulfates via Nucleophilic Radiofluorination

Sulfuryl fluoride gas is a key reagent for SO2F transfer. However, conventional SO2F transfer reactions have limited 18F-radiochemistry translation, due to the inaccessibility of gaseous [18F]­SO2F2. Herein, we report the first SO2F2-free synthesis of aryl [18F]­fluorosulfates from both phenolic and...

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Veröffentlicht in:Organic letters 2020-07, Vol.22 (14), p.5511-5516
Hauptverfasser: Kwon, Young-Do, Jeon, Min Ho, Park, Nam Kyu, Seo, Jeong Kon, Son, Jeongmin, Ryu, Young Hoon, Hong, Sung You, Chun, Joong-Hyun
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Sprache:eng
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Zusammenfassung:Sulfuryl fluoride gas is a key reagent for SO2F transfer. However, conventional SO2F transfer reactions have limited 18F-radiochemistry translation, due to the inaccessibility of gaseous [18F]­SO2F2. Herein, we report the first SO2F2-free synthesis of aryl [18F]­fluorosulfates from both phenolic and isolated aryl imidazylate precursors with cyclotron-produced 18F–. The radiochemical yields ranged from moderate to good with excellent functional group tolerance. The reliability of our approach was validated by the automated radiosynthesis of 4-acetamidophenyl [18F]­fluorosulfate.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01868