Rhodium-catalyzed [2+2+2] cycloaddition of various fluorine-containing alkynes--novel synthesis of multi-substituted fluoroalkylated aromatic compounds

Org Biomol Chem. 2010 Apr 7;8(7):1718-24. doi: 10.1039/b926192c. Epub 2010 Feb 22.

Abstract

Treatment of various fluorinated internal alkynes with 10 mol% of RhCl(3).H(2)O and 30 mol% of i-Pr(2)NEt in toluene at the reflux temperature for 18 h gave the corresponding trimerization products as an isomeric mixture in high yields. Cycloaddition using 1.0 equiv. of fluorinated alkynes and 2.0 equiv. of non-fluorinated alkynes under the same reaction conditions as in the trimerization led to mono- and bis-fluoroalkylated benzene derivatives in high yields, together with small amounts of trimerization products. The reaction of fluorine-containing bispropargyl ether with non-fluorinated alkynes took place smoothly to afford the corresponding bicyclic molecules in good to high yields.

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Catalysis
  • Cyclization
  • Fluorine Compounds / chemical synthesis*
  • Fluorine Compounds / chemistry
  • Hydrocarbons, Aromatic / chemical synthesis*
  • Hydrocarbons, Aromatic / chemistry
  • Rhodium / chemistry*

Substances

  • Alkynes
  • Fluorine Compounds
  • Hydrocarbons, Aromatic
  • Rhodium