Diphenyliodonium-Catalyzed Fluorination of Arynes: Synthesis of ortho-Fluoroiodoarenes

Angew Chem Int Ed Engl. 2015 Sep 7;54(37):10773-7. doi: 10.1002/anie.201503308. Epub 2015 Jul 23.

Abstract

Described is a one-pot vicinal fluorination-iodination of arynes at room temperature. The diphenyliodonium salt proved to be a privileged catalyst for this nucleophilic fluorination process using CsF as a fluorine source, and a subsequent facile electrophilic iodination with C4 F9 I was also found to be crucial to ensure the efficient fluorination. This new synthetic protocol has a broad substrate scope under mild reaction conditions.

Keywords: Lewis acids; arynes; fluorine; hypervalent compounds; synthetic methods.

MeSH terms

  • Biphenyl Compounds / chemistry*
  • Catalysis
  • Fluorine / chemistry*
  • Hydrocarbons / chemical synthesis*
  • Onium Compounds / chemistry*
  • Proton Magnetic Resonance Spectroscopy

Substances

  • Biphenyl Compounds
  • Hydrocarbons
  • Onium Compounds
  • diphenyliodonium
  • Fluorine