Efficient synthesis of alkyl aryl ketones & ketals via palladium-catalyzed regioselective arylation of vinyl ethers

Org Biomol Chem. 2010 May 7;8(9):2012-5. doi: 10.1039/c001004a. Epub 2010 Mar 22.

Abstract

The combination of Pd(OAc)(2) with 1,3-bis(diphenylphosphino)propane (dppp) in ethylene glycol constitutes a high-performance catalytic system for highly regioselective arylation of a range of electron-rich vinyl ethers by aryl bromides to provide, upon hydrolysis, alkyl aryl ketones and cyclic ketals in good yields with up to 3.75 x 10(5) TON and 15625 h(-1) TOF.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Catalysis
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Vinyl Compounds / chemistry*

Substances

  • Acetates
  • Ketones
  • Organometallic Compounds
  • Vinyl Compounds
  • palladium(II) acetate
  • vinyl ether