Microwave-promoted Pd-catalyzed cyanation of aryl triflates: a fast and versatile access to 3-cyano-3-desoxy-10-ketomorphinans

Org Lett. 2003 Jan 23;5(2):201-3. doi: 10.1021/ol027256p.

Abstract

[reaction: see text] A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph(3)P)(4) as the catalyst and 2.0 equiv of Zn(CN)(2) as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy-10-ketomorphinans. The reaction was generally completed in 15 min at 200 degrees C and produced products in greater than 86% yields.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Cyanides / chemistry
  • Ligands
  • Mesylates / chemistry
  • Microwaves
  • Narcotic Antagonists*
  • Nitriles / chemical synthesis*
  • Palladium
  • Receptors, Opioid / agonists*

Substances

  • Cyanides
  • Ligands
  • Mesylates
  • Narcotic Antagonists
  • Nitriles
  • Receptors, Opioid
  • Palladium
  • trifluoromethanesulfonic acid