Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium

J Am Chem Soc. 2015 May 6;137(17):5686-94. doi: 10.1021/jacs.5b02659. Epub 2015 Apr 22.

Abstract

Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [(18)F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this report, we demonstrate the possibility of (18)F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile-thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [(18)F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. The substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetonitriles / chemistry
  • Alcohols / chemistry
  • Catalysis
  • Fluorine Radioisotopes / chemistry*
  • Molecular Structure
  • Nanoparticles / chemistry
  • Titanium / chemistry*
  • Tosyl Compounds / chemical synthesis*
  • Tosyl Compounds / chemistry
  • Water / chemistry

Substances

  • Acetonitriles
  • Alcohols
  • Fluorine Radioisotopes
  • Tosyl Compounds
  • Water
  • titanium dioxide
  • Titanium
  • acetonitrile