A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging

Lee, Eunsung; Kamlet, Adam S.; Powers, David C.; Neumann, Constanze N.; Boursalian, Gregory B.; Furuya, Takeru; Choi, Daniel C.; Hooker, Jacob M.; Ritter, Tobias

doi:10.1126/science.1212625

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A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging

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https://science.sciencemag.org/content/sci/334/6056/639.full.pdf
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Lee, E., Kamlet, A. S., Powers, D. C., Neumann, C. N., Boursalian, G. B., Furuya, T., et al. (2011). A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging. Science, 334(6056), 639-642. doi:10.1126/science.1212625.

Cite as: https://hdl.handle.net/21.11116/0000-0008-F376-1

Abstract

The unnatural isotope fluorine-18 (¹⁸F) is used as a positron emitter in molecular imaging. Currently, many potentially useful ¹⁸F-labeled probe molecules are inaccessible for imaging because no fluorination chemistry is available to make them. The 110-minute half-life of ¹⁸F requires rapid syntheses for which [¹⁸F]fluoride is the preferred source of fluorine because of its practical access and suitable isotope enrichment. However, conventional [¹⁸F]fluoride chemistry has been limited to nucleophilic fluorination reactions. We report the development of a palladium-based electrophilic fluorination reagent derived from fluoride and its application to the synthesis of aromatic ¹⁸F-labeled molecules via late-stage fluorination. Late-stage fluorination enables the synthesis of conventionally unavailable positron emission tomography (PET) tracers for anticipated applications in pharmaceutical development as well as preclinical and clinical PET imaging.