Nickel-catalyzed three-component domino reactions of aryl Grignard reagents, alkynes, and aryl halides producing tetrasubstituted alkenes

J Am Chem Soc. 2015 Mar 11;137(9):3189-92. doi: 10.1021/ja513166w. Epub 2015 Feb 27.

Abstract

Three-component reaction of aryl Grignard reagents, alkynes, and aryl halides in the presence of 1 mol % of NiCl2 proceeded sequentially through carbomagnesiation of the alkyne followed by cross-coupling of the resulting alkenyl Grignard reagent with aryl halide to give tetrasubstituted alkenes in high yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Nickel / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • nickel chloride
  • Nickel