Formation of quaternary carbon center with a trifluoromethyl group using a Pd-catalyzed allylation reaction

Chem Pharm Bull (Tokyo). 2007 Nov;55(11):1593-6. doi: 10.1248/cpb.55.1593.

Abstract

Synthesis of compounds with quaternary carbons is one of the most attractive reactions in the synthetic chemistry. However, there are only a few reports on synthesis of the compounds with a fluoroalkyl group at a quaternary carbon center. Recently, we reported the synthesis of alpha-trifluoromethylated ketones by the reaction of alpha,beta-unsaturated ketones with CF(3)-I using a Rh catalyst. When the alpha-trifluoromethylated ketones and allyl carbonates were treated with a Pd catalyst, the allylation reaction proceeded smoothly at the trifluoromethylated carbon to give the desired compounds with a trifluoromethylated quaternary carbon center in good to excellent yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Chlorofluorocarbons, Methane / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Ketones / chemical synthesis*
  • Models, Chemical
  • Palladium / chemistry*

Substances

  • Allyl Compounds
  • Chlorofluorocarbons, Methane
  • Hydrocarbons, Fluorinated
  • Ketones
  • Palladium
  • Carbon
  • fluoroform