Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins

Thomas J.A. Graham, R. Frederick Lambert, Karl Ploessl, Hank F. Kung, Abigail G. Doyle

Research output: Contribution to journalArticlepeer-review

77 Scopus citations


Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [18F](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [18F]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.

Original languageEnglish (US)
Pages (from-to)5291-5294
Number of pages4
JournalJournal of the American Chemical Society
Issue number14
StatePublished - Apr 9 2014

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Biochemistry
  • Catalysis
  • Colloid and Surface Chemistry


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