Rapid Syntheses of [11C]Arylvinyltrifluoromethanes through Treatment of (E)-Arylvinyl(phenyl)iodonium Tosylates with [11C]Trifluoromethylcopper(I)

Org Lett. 2020 Jun 5;22(11):4574-4578. doi: 10.1021/acs.orglett.0c01705. Epub 2020 May 27.

Abstract

We report a method for labeling arylvinyltrifluoromethanes with carbon-11 (t1/2 = 20.4 min) as representatives of a new radiolabeled chemotype that has potential for developing radiotracers for biomedical imaging with positron emission tomography. Treatment of (E)-arylvinyl(phenyl)iodonium tosylates (1a-1k) with [11C[CuCF3 gave the corresponding [11C]arylvinyltrifluoromethanes ([11C]2a-[11C]2k) in high radiochemical yields (90-97%) under rapid (2 min) and mild (60 °C) conditions.

Publication types

  • Research Support, N.I.H., Intramural

MeSH terms

  • Carbon Radioisotopes
  • Chlorofluorocarbons, Methane / chemical synthesis*
  • Chlorofluorocarbons, Methane / chemistry
  • Hydrocarbons, Iodinated / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Tosyl Compounds / chemistry*

Substances

  • Carbon Radioisotopes
  • Carbon-11
  • Chlorofluorocarbons, Methane
  • Hydrocarbons, Iodinated
  • Organometallic Compounds
  • Tosyl Compounds
  • trifluoromethylcopper