Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles

Org Lett. 2013 Feb 15;15(4):788-91. doi: 10.1021/ol303440y. Epub 2013 Jan 25.

Abstract

An efficient palladium-catalyzed synthesis of 3-acylindoles using free (N-H) indoles and nitriles has been developed. The acylation reaction proceeded well under the Pd(OAc)(2)/2,2'-bipyridine system and with D-(+)-camphorsulfonic acid as the additive. A possible mechanism involving carbopalladation of nitriles and subsequent hydrolysis of ketimines is proposed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Molecular Structure
  • Nitriles / chemistry*
  • Palladium / chemistry*

Substances

  • Indoles
  • Nitriles
  • Palladium