Login / Signup

Photocatalytic Decarboxylative Coupling of Aliphatic N-hydroxyphthalimide Esters with Polyfluoroaryl Nucleophiles.

Xiangli YiRunze MaoLara LavrencicXile Hu
Published in: Angewandte Chemie (International ed. in English) (2021)
Polyfluoroarenes are an important class of compounds in medical and material chemistry. The synthesis of alkylated polyfluoroarenes remains challenging. Here we describe a decarboxylative coupling reaction of N-hydroxyphthalimide esters of aliphatic carboxylic acids with polyfluoroaryl zinc reagents (Zn-ArF ) via synergetic photoredox and copper catalysis. This method readily converts primary and secondary alkyl carboxylic acids into the corresponding polyfluoroaryl compounds, which could have a wide range of F-content (2F-5F) and variable F-substitution patterns on the aryl groups. Broad scope and good functional group compatibility were achieved, including on substrates derived from natural products and pharmaceuticals. Mechanistic study revealed that a [Cu-(ArF )2 ] species could be responsible for the transfer of polyfluoroaryl groups to the alkyl radicals.
Keyphrases
  • visible light
  • electron transfer
  • room temperature
  • healthcare
  • oxide nanoparticles
  • single cell
  • ionic liquid
  • drug discovery
  • risk assessment
  • gold nanoparticles