One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol

Org Biomol Chem. 2011 Dec 21;9(24):8328-39. doi: 10.1039/c1ob06372c. Epub 2011 Nov 7.

Abstract

Difluoroalkenylzinc reagents prepared from 1-(2'-methoxy-ethoxymethoxy)-2,2,2-trifluoroethane and 1-(N,N-diethylcarbamoyloxy)-2,2,2-trifluoroethane at ice bath temperatures underwent Negishi coupling with a range of aryl halides in a convenient one pot procedure. While significant differences between the enol acetal and carbamate reagents were revealed, the Negishi protocol compared very favourably with alternative coupling procedures in terms of overall yields from trifluoroethanol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Hydrocarbons, Fluorinated / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Stereoisomerism
  • Temperature*
  • Trifluoroethanol / chemistry*

Substances

  • Hydrocarbons, Fluorinated
  • Organometallic Compounds
  • Trifluoroethanol