Pd(0)-Mediated 11C-Carbonylation of Aryl(mesityl)iodonium Salts as a Route to [11C]Arylcarboxylic Acids and Derivatives

J Org Chem. 2017 Nov 17;82(22):11925-11932. doi: 10.1021/acs.joc.7b01704. Epub 2017 Oct 13.

Abstract

Pd(0)-mediated 11C-carbonylation of aryl(mesityl)iodonium salts followed by suitable quench provides a rapid room-temperature two-pot procedure for labeling arylcarboxylic acids and amide derivatives with the short-lived positron emitter carbon-11 (t1/2 = 20.4 min) in generally good to high yields (up to 71%). High product ring selectivity (≥13) was achieved when using mesityl as a spectator group in the diaryliodonium salt precursors. This process has potential for preparing new radiotracers for molecular imaging with positron emission tomography.

Publication types

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

MeSH terms

  • Carbon Isotopes
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Catalysis
  • Hydrocarbons, Iodinated / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Salts / chemistry

Substances

  • Carbon Isotopes
  • Carboxylic Acids
  • Hydrocarbons, Iodinated
  • Organometallic Compounds
  • Salts
  • Palladium