Hypervalent iodine-promoted α-fluorination of acetophenone derivatives with a triethylamine·HF complex

J Org Chem. 2014 Jun 20;79(12):5842-6. doi: 10.1021/jo500691b. Epub 2014 May 30.

Abstract

The direct fluorination reaction of acetophenone using iodosylarenes and TEA·5HF was conducted under mild conditions except for use of a HF reagent. The fluorination reaction was applied to acetophenone derivatives, acetonaphthones, benzyl phenyl ketone, propiophenone, butyrophenone, 1-indanone, and phenacyl chloride, giving selectively the corresponding α-fluoroketone derivatives in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemical synthesis*
  • Acetophenones / chemistry
  • Ethylamines / chemistry*
  • Halogenation
  • Hydrocarbons, Fluorinated / chemistry*
  • Indicators and Reagents / chemistry
  • Iodine / chemistry*
  • Molecular Structure

Substances

  • Acetophenones
  • Ethylamines
  • Hydrocarbons, Fluorinated
  • Indicators and Reagents
  • Iodine
  • acetophenone
  • triethylamine