Palladium-catalyzed cross-coupling reaction of diazo compounds and vinyl boronic acids: an approach to 1,3-diene compounds

J Org Chem. 2014 Aug 15;79(16):7711-7. doi: 10.1021/jo5012703. Epub 2014 Jul 24.

Abstract

A palladium-catalyzed oxidative cross-coupling of vinyl boronic acids and cyclic α-diazocarbonyl compounds has been reported. The reaction constitutes an efficient method for the synthesis of 1,3-diene compounds bearing a ring structure. Mechanistically, the reaction involves migratory insertion of palladium carbene as the key step.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkenes / chemistry
  • Azo Compounds / chemistry*
  • Boronic Acids / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Palladium / chemistry*
  • Vinyl Compounds / chemistry*

Substances

  • Alkenes
  • Azo Compounds
  • Boronic Acids
  • Vinyl Compounds
  • carbene
  • Palladium
  • Methane