A new access to 4 H-quinolizines from 2-vinylpyridine and alkynes promoted by rhodium-N-heterocyclic-carbene catalysts

Chemistry. 2013 Mar 18;19(12):3812-6. doi: 10.1002/chem.201300236. Epub 2013 Feb 21.

Abstract

Forging the lock that autolocks! Rh-NHC catalysts promote a new access to 4 H-quinolizine species from 2-vinylpyridine and terminal and internal alkynes through C-H activation and C-C coupling reactions (see figure). N-Bridgehead heterocycle formation is favored for internal- over terminal-substituted butadienylpyridine derivatives in a thermal 6π-electrocyclization process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis
  • Alkynes / chemistry*
  • Catalysis
  • Coordination Complexes / chemistry*
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*
  • Quinolizines / chemical synthesis*
  • Quinolizines / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Coordination Complexes
  • Pyridines
  • Quinolizines
  • carbene
  • Rhodium
  • 2-vinylpyridine
  • Methane