Copper-catalyzed intermolecular and regioselective aminofluorination of styrenes: facile access to β-fluoro-N-protected phenethylamines

Chem Commun (Camb). 2015 Feb 25;51(16):3379-82. doi: 10.1039/c4cc10162f.

Abstract

A copper-catalyzed regio- and intermolecular aminofluorination of styrenes has been developed. In this reaction Ph-I=N-Ts and Et3N·3HF act as nitrogen and fluorine sources, respectively. The obtained β-fluoro-N-Ts-phenethylamines can be N-alkylated with subsequent deprotection affording the corresponding β-fluoro-N-alkylated phenethylamines, which are interesting building blocks for compounds acting on neuronal targets.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Fluorine / chemistry*
  • Phenethylamines / chemistry*
  • Stereoisomerism
  • Styrenes / chemistry*

Substances

  • Phenethylamines
  • Styrenes
  • Fluorine
  • phenethylamine
  • Copper