One-pot synthesis of diarylmethanones through palladium-catalyzed sequential coupling and aerobic oxidation of aryl bromides with acetophenone as a latent carbonyl donor

J Org Chem. 2014 Jul 18;79(14):6554-62. doi: 10.1021/jo5010185. Epub 2014 Jul 8.

Abstract

A one-pot palladium-catalyzed synthesis of symmetrical and unsymmetrical diarylmethanones using acetophenone and aryl bromides as raw materials has been developed. In this reaction, acetophenone acts as a latent carbonyl donor and two pathways of palladium-catalyzed sequential coupling and aerobic oxidation are identified. The reaction is applicable to a spectrum of substrates and delivers the products in moderate to good yields. This method can be used for the synthesis of ketoprofen, a nonsteroidal anti-inflammatory drug, in a two-step procedure and 45% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetophenones / chemistry*
  • Catalysis
  • Hydrocarbons, Brominated / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Palladium / chemistry*

Substances

  • Acetophenones
  • Hydrocarbons, Brominated
  • Ketones
  • Organometallic Compounds
  • Palladium
  • acetophenone