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. 2021 Feb 5;23(3):1011-1015.
doi: 10.1021/acs.orglett.0c04209. Epub 2021 Jan 25.

A General Protocol for Cu-Mediated Fluoro-deamination: Sandmeyer Fluorination of Diverse Aromatic Substrates

R Manuel Pérez-García  1 , Gaute Grønnevik  1 , Patrick J Riss  1
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Free PMC article

A General Protocol for Cu-Mediated Fluoro-deamination: Sandmeyer Fluorination of Diverse Aromatic Substrates

R Manuel Pérez-García et al. Org Lett. .
Free PMC article

Abstract

A Cu(I)-mediated fluoro-deamination method for nucleophilic radiofluorination was devised. The method affords fluorinated aromatic products directly from anilines under both no-carrier added and stoichiometric conditions. Isolated radiochemical yields range from 11% to 81% with high radiochemical purities and a molar activity of 58 MBq/nmol. The reaction conditions were implemented successfully in an automated process for production of (S)-4[18F]fluorogluthetimide on a radiosynthesis module.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Modern Methods for Fluoro-deamination Reactions (SAX, Strong Anion Exchanger; SCX, Strong Cation Exchanger)
Scheme 2
Scheme 2. Synthesis of Labelled Aldehyde [18F]14 and the Radiotracer Candidate [18F]18
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References

    1. Lee E.; Kamlet A. S.; Powers D. C.; Neumann C. N.; Boursalian G. B.; Furuya T.; Choi D. C.; Hooker J. M.; Ritter T. A fluoride-derived electrophilic late-stage fluorination reagent for PET imaging. Science 2011, 334, 639.10.1126/science.1212625. - DOI - PMC - PubMed
    1. Lee E.; Hooker J. M.; Ritter T. Nickel-mediated oxidative fluorination for PET with aqueous [18F]fluoride. J. Am. Chem. Soc. 2012, 134, 17456.10.1021/ja3084797. - DOI - PMC - PubMed
    1. Ichiishi N.; Brooks A. F.; Topczewski J. J.; Rodnick M. E.; Sanford M. E.; Scott P. J. H. Copper-catalyzed [18F]fluorination of (mesityl)(aryl)iodonium salts. Org. Lett. 2014, 16, 3224.10.1021/ol501243g. - DOI - PMC - PubMed
    1. Tredwell M.; Preshlock S. M.; Taylor N. J.; Gruber S.; Huiban M.; Passchier J.; Mercier J.; Génicot C.; Gouverneur V. A general copper-mediated nucleophilic 18F fluorination of arenes. Angew. Chem., Int. Ed. 2014, 53, 7751.10.1002/anie.201404436. - DOI - PubMed
    1. Mossine A. V.; Brooks A. F.; Makaravage K. J.; Miller J. M.; Ichiishi N.; Sanford M. S.; Scott P. J. H. Synthesis of [18F]arenes via the copper-mediated [18F]fluorination of boronic acids. Org. Lett. 2015, 17, 5780.10.1021/acs.orglett.5b02875. - DOI - PMC - PubMed

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