A simple method for the electrophilic cyanation of secondary amines

Org Lett. 2014 Jan 3;16(1):247-9. doi: 10.1021/ol403245r. Epub 2013 Dec 6.

Abstract

Bleach oxidizes trimethylsilyl cyanide to generate an electrophilic cyanating reagent that readily reacts with an amine nucleophile. This oxidative N-cyanation reaction allows for the preparation of disubstituted cyanamides from amines without using highly toxic cyanogen halides.

Publication types

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

MeSH terms

  • Amines / chemistry*
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry

Substances

  • Amines
  • Nitriles