anti-Markovnikov hydroamination of alkenes catalyzed by a two-component organic photoredox system: direct access to phenethylamine derivatives

Angew Chem Int Ed Engl. 2014 Jun 10;53(24):6198-201. doi: 10.1002/anie.201402443. Epub 2014 Apr 24.

Abstract

Disclosed herein is a general catalytic system for the intermolecular anti-Markovnikov hydroamination of alkenes. By using an organocatalytic photoredox system, α- and β-substituted styrenes as well as aliphatic alkenes undergo anti-Markovnikov hydroamination. Heterocyclic amines were also successfully employed as nitrogen nucleophiles, thus providing a direct route to heterocyclic motifs common in medicinal agents.

Keywords: alkenes; amines; organocatalysis; photochemistry; radicals.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Molecular Structure
  • Phenethylamines / chemistry*
  • Photochemistry

Substances

  • Alkenes
  • Phenethylamines