Copper-catalyzed decarboxylative C-P cross-coupling of alkynyl acids with H-phosphine oxides: a facile and selective synthesis of (E)-1-alkenylphosphine oxides

Org Lett. 2014 Sep 5;16(17):4464-7. doi: 10.1021/ol502009b. Epub 2014 Aug 21.

Abstract

A novel and efficient copper-catalyzed decarboxylative cross-coupling of alkynyl acids for the stereoselective synthesis of E-alkenylphosphine oxides has been developed. In the presence of 10 mol % of CuCl without added ligand, base, and additive, various alkynyl acids reacted with H-phosphine oxides to afford E-alkenylphosphine oxides with operational simplicity, broad substrate scope, and the stereoselectivity for E-isomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Alkynes / chemical synthesis
  • Alkynes / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Decarboxylation
  • Esters
  • Oxides / chemical synthesis*
  • Oxides / chemistry
  • Phosphines / chemical synthesis*
  • Phosphines / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • Carboxylic Acids
  • Esters
  • Oxides
  • Phosphines
  • Copper