Metal-free oxidative olefination of primary amines with benzylic C-H bonds through direct deamination and C-H bond activation

Org Biomol Chem. 2014 Sep 14;12(34):6557-60. doi: 10.1039/c4ob01025f.

Abstract

An oxidative olefination reaction between aliphatic primary amines and benzylic sp(3) C-H bonds has been achieved using N-bromosuccinimide as catalyst and tert-butyl hydroperoxide as oxidant. The olefination proceeds under mild metal-free conditions through direct deamination and benzylic C-H bond activation, and provides easy access to biologically active 2-styrylquinolines with (E)-configuration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amines / chemistry*
  • Bromosuccinimide / chemistry
  • Catalysis
  • Deamination
  • Oxidants / chemistry*
  • Oxidation-Reduction
  • Quinolines / chemical synthesis*
  • tert-Butylhydroperoxide / chemistry*

Substances

  • Alkenes
  • Amines
  • Oxidants
  • Quinolines
  • tert-Butylhydroperoxide
  • Bromosuccinimide