Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids

Org Lett. 2015 Dec 4;17(23):5780-3. doi: 10.1021/acs.orglett.5b02875. Epub 2015 Nov 14.

Abstract

A copper-mediated radiofluorination of aryl- and vinylboronic acids with K(18)F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [(18)F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.

Publication types

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

MeSH terms

  • Boronic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Fluorine Radioisotopes / chemistry*
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Positron-Emission Tomography
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry

Substances

  • 3-fluoro-5-((pyridin-3-yl)ethynyl)benzonitrile
  • Boronic Acids
  • Fluorine Radioisotopes
  • Nitriles
  • Pyridines
  • Radiopharmaceuticals
  • Copper