Palladium- and nickel-catalyzed Kumada cross-coupling reactions of gem-difluoroalkenes and monofluoroalkenes with Grignard reagents

J Org Chem. 2014 Nov 7;79(21):10537-46. doi: 10.1021/jo5022234. Epub 2014 Oct 27.

Abstract

A novel Kumada-Tamao-Corriu cross-coupling reaction of gem-di- or monofluoroalkenes with Grignard reagents, with or without β-hydrogen atoms, in the presence of a catalytic amount of palladium- or nickel-based catalysts has been developed. The reaction is performed under mild conditions (room temperature or reflux in diethyl ether for 1-2 h) and leads to di-cross- or mono-cross-coupled products in good to high yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Hydrocarbons, Fluorinated / chemistry*
  • Indicators and Reagents / chemistry*
  • Molecular Structure
  • Nickel / chemistry*
  • Palladium / chemistry*

Substances

  • Alkenes
  • Hydrocarbons, Fluorinated
  • Indicators and Reagents
  • Palladium
  • Nickel