Selective palladium-catalyzed C-F activation/carbon-carbon bond formation of polyfluoroaryl oxazolines

J Org Chem. 2012 Feb 17;77(4):1798-804. doi: 10.1021/jo2023262. Epub 2012 Feb 8.

Abstract

A selective palladium-catalyzed Suzuki-Miyaura coupling reaction of polyfluorophenyl oxazolines through ortho C-F activation is described. It was found that reactions with DPPF as the ligand occurred much faster than those with other ligands. A variety of arylboronic acids including challenging functionalized arylboronic acids such as enolizable ketones, aldehyde, cyano, ester, and trifluoromethyl groups were tolerated with the reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Boronic Acids / chemistry
  • Carbon / chemistry*
  • Catalysis
  • Esters / chemistry
  • Fluorine / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Ketones / chemistry
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Palladium / chemistry*

Substances

  • Aldehydes
  • Boronic Acids
  • Esters
  • Hydrocarbons, Fluorinated
  • Ketones
  • Ligands
  • Oxazoles
  • Fluorine
  • Palladium
  • Carbon