4.8 Article

Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic 18F-Fluorination

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 35, Pages 11125-11132

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b06730

Keywords

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Funding

  1. European Union's Seventh Framework Programme (FP7/2007-2013) [602102]
  2. Leonard Wolfson Experimental Neurology Centre, Mallinckrodt
  3. UCL Business [HFSE PoC-13-003]
  4. Wellcome Trust [102407/Z/13/Z]
  5. Clinical Research and Development Committee Research Funding from the BRC/UCLH Charities [F196]
  6. CRUK & EPSRC Comprehensive Cancer Imaging Centre at KCL & UCL - Cancer Research UK [C1519/A16463]
  7. CRUK & EPSRC Comprehensive Cancer Imaging Centre at KCL & UCL - Engineering and Physical Sciences Research Council (EPSRC) [C1519/A16463]
  8. EPSRC Case Studentship
  9. GE
  10. UCL MSci in Chemistry
  11. UCL MRes Organic Chemistry: Drug Discovery Programme
  12. Reta Lila Weston Institute for Neurological Studies
  13. Progressive Supra nuclear Palsy (Europe) Association
  14. Department of Health's NIHR Biomedical Research Centres funding scheme
  15. EPSRC [EP/K005030/1, EP/P020410/1] Funding Source: UKRI
  16. Wellcome Trust [102407/Z/13/Z] Funding Source: Wellcome Trust

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Herein, we report a novel intramolecular ring-closing reaction of biaryl thioethers that give access to highly functionalized dibenzothiophene sulfonium salts under mild conditions. The resulting precursors react regioselectively with [F-18]fluoride to give [F-18]fluoroarenes in predictable radiochemical yields. The strategy expands the available radiochemical space and provides superior labeling efficiency for clinically relevant PET tracers.

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