A practical synthesis of alpha-aryl methyl ketones via a transition-metal-free Meerwein arylation

J Org Chem. 2007 Mar 2;72(5):1856-8. doi: 10.1021/jo062483g. Epub 2007 Jan 31.

Abstract

We report herein a simple, scalable, transition-metal-free approach to the synthesis of alpha-aryl methyl ketones from diazonium tetrafluoroborate salts under mild conditions. This methodology uses easily accessible and nontoxic starting material and was applied to the multi-kilogram-scale preparation of 1-(3-bromo-4-methylphenyl)propan-2-one.

MeSH terms

  • Catalysis
  • Chromatography, High Pressure Liquid
  • Hydrocarbons, Brominated / chemical synthesis
  • Ketones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Metals / chemistry
  • Propane / analogs & derivatives
  • Propane / chemical synthesis
  • Solvents
  • Spectrometry, Mass, Electrospray Ionization
  • Transition Elements / chemistry*

Substances

  • 1-(3-bromo-4-methylphenyl)propan-2-one
  • Hydrocarbons, Brominated
  • Ketones
  • Metals
  • Solvents
  • Transition Elements
  • Propane