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Tandem Iridium-Catalyzed C–H Borylation/Copper-Mediated Radiofluorination of Aromatic C–H Bonds with [18F]TBAF

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Positron Emission Tomography

Part of the book series: Methods in Molecular Biology ((MIMB,volume 2729))

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Abstract

Direct C–H functionalization of (hetero)aromatic C–H bonds with iridium-catalyzed borylation followed by copper-mediated radiofluorination of the in situ generated organoboronates affords fluorine-18 labeled aromatics in high radiochemical conversions and meta-selectivities. This protocol describes the benchtop reaction assembly of the C–H borylation and radiofluorination steps, which can be utilized for the fluorine-18 labeling of densely functionalized bioactive scaffolds.

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Author information

Authors and Affiliations

  1. Department of Chemistry, University of Michigan, Ann Arbor, MI, USA

    Maria Morales, Liam S. Sharninghausen & Melanie S. Sanford

  2. Department of Radiology, University of Michigan, Ann Arbor, MI, USA

    Sean Preshlock, Jay S. Wright, Allen F. Brooks & Peter J. H. Scott

Authors
  1. Maria Morales
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  2. Sean Preshlock
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  3. Liam S. Sharninghausen
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  4. Jay S. Wright
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  5. Allen F. Brooks
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  6. Melanie S. Sanford
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  7. Peter J. H. Scott
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Corresponding author

Correspondence to Peter J. H. Scott .

Editor information

Editors and Affiliations

  1. School of Biomedical Engineering and Imaging Sciences, King’s College London, London, UK

    Timothy H. Witney

  2. Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, ON, Canada

    Adam J. Shuhendler

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© 2024 The Author(s), under exclusive license to Springer Science+Business Media, LLC, part of Springer Nature

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Morales, M. et al. (2024). Tandem Iridium-Catalyzed C–H Borylation/Copper-Mediated Radiofluorination of Aromatic C–H Bonds with [18F]TBAF. In: Witney, T.H., Shuhendler, A.J. (eds) Positron Emission Tomography. Methods in Molecular Biology, vol 2729. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-3499-8_4

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  • DOI: https://doi.org/10.1007/978-1-0716-3499-8_4

  • Published:

  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-0716-3498-1

  • Online ISBN: 978-1-0716-3499-8

  • eBook Packages: Springer Protocols

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