Copper-catalyzed regioselective ortho C-H cyanation of vinylarenes

Angew Chem Int Ed Engl. 2014 Aug 11;53(33):8677-81. doi: 10.1002/anie.201402449. Epub 2014 May 6.

Abstract

A copper-based catalytic technique for the regioselective ortho C-H cyanation of vinylarenes has been developed. This method provides an effective means for the selective functionalization of vinylarene derivatives. A copper-catalyzed cyanative dearomatization mechanism is proposed to account for the regiochemical course of this reaction.

Keywords: CH activation; copper; dearomatization; ligand design; synthetic methods.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkenes / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Copper / chemistry*
  • Cyanates / chemistry
  • Hydrogen / chemistry
  • Hydrogenation
  • Kinetics
  • Stereoisomerism
  • Temperature
  • Thermodynamics

Substances

  • Alkenes
  • Cyanates
  • Carbon
  • Copper
  • Hydrogen