Hydrophosphinylation of unactivated terminal alkenes catalyzed by nickel chloride

J Org Chem. 2013 Jul 5;78(13):6599-608. doi: 10.1021/jo4008749. Epub 2013 Jun 18.

Abstract

The room-temperature hydrophosphinylation of unactivated monosubstituted alkenes using phosphinates (ROP(O)H2) and catalytic NiCl2 in the presence of dppe is described. The method is competitive with prior palladium-catalyzed reactions and uses a much cheaper catalyst and simple conditions. The scope of the reaction is quite broad in terms of unactivated terminal olefins, proceeds at room temperature, often avoids chromatographic purification, and allows one-pot conversion to various organophosphorus compounds.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Molecular Structure
  • Nickel / chemistry*
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • Phosphinic Acids / chemistry

Substances

  • Alkenes
  • Organophosphorus Compounds
  • Phosphinic Acids
  • nickel chloride
  • Nickel