Palladium-mediated 11C-carbonylations using aryl halides and cyanamide

Org Biomol Chem. 2017 Jun 7;15(22):4875-4881. doi: 10.1039/c7ob01064h.

Abstract

A robust and high-yielding radiochemical synthesis of 11C-N-cyanobenzamides using a palladium-mediated aminocarbonylation with 11C-CO, aryl halides and cyanamide is described. The bidentate ligand 1,1'-bis(diphenylphosphino)ferrocene provided 11C-N-cyanobenzamides from aryl-iodides, bromides, triflates and even chlorides in 28-79% radiochemical yield after semi-preparative HPLC. To further highlight the utility of this method, novel 11C-N-cyanobenzamide analogs of flufenamic acid, meflanamic acid, dazoxiben and tamibarotene were synthesized in 34-71% radiochemical yields.

MeSH terms

  • Benzamides / chemical synthesis*
  • Benzamides / chemistry
  • Cyanamide / chemistry*
  • Hydrocarbons, Halogenated / chemistry*
  • Molecular Structure
  • Palladium / chemistry*

Substances

  • Benzamides
  • Hydrocarbons, Halogenated
  • Cyanamide
  • Palladium