Selective anti-Markovnikov cyclization and hydrofluorination reaction in superacid HF/SbF5: a tool in the design of nitrogen-containing (fluorinated) polycyclic systems

J Org Chem. 2013 May 3;78(9):4463-72. doi: 10.1021/jo400398y. Epub 2013 Apr 24.

Abstract

The selective synthesis of tetrahydroquinolines and fluorinated arylamines was performed in superacid HF/SbF5 through a superelectrophilic ammonium-carbenium activation process. This anti-Markovnikov oriented reaction was applied to the straightforward synthesis of highly valued (fluorinated) nitrogen-containing heterocyclic compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antimony / chemistry*
  • Cyclization
  • Drug Design*
  • Fluorides / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrofluoric Acid / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*
  • Polycyclic Compounds / chemistry
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry

Substances

  • Hydrocarbons, Fluorinated
  • Polycyclic Compounds
  • Quinolines
  • antimony pentafluoride
  • Antimony
  • 1,2,3,4-tetrahydroquinoline
  • Fluorides
  • Hydrofluoric Acid