Copper-catalyzed trifluoromethylation-cyclization of enynes: highly regioselective construction of trifluoromethylated carbocycles and heterocycles

Chemistry. 2013 Oct 18;19(43):14420-4. doi: 10.1002/chem.201303025. Epub 2013 Sep 23.

Abstract

Regioselective trifluoromethylation-cyclization: A method for copper-catalyzed trifluoromethylation-cyclization of simple enynes using the CC triple bond as a nucleophile is reported for the first time. The reaction proceeds efficiently in a highly regioselective manner to give various 5- or 6-exo-dig carbocycles and heterocycles in moderate to high yields.

Keywords: copper; cyclization; enynes; regioselectivity; trifluoromethylation.

Publication types

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

MeSH terms

  • Alkynes / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Copper / chemistry
  • Cyclization
  • Fluorine / chemistry*
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Methylation
  • Stereoisomerism

Substances

  • Alkynes
  • Heterocyclic Compounds
  • Fluorine
  • Carbon
  • Copper