A novel and convenient synthesis of benzonitriles: Electrophilic cyanation of aryl and heteroaryl bromides

Pazhamalai Anbarasan, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

119 Scopus citations

Abstract

N-Cyano-N-phenyl-p-methylbenzenesulfonamide has been used as a more benign electrophilic cyanation reagent for the synthesis of various benzonitriles from (hetero)aryl bromides via formation of Grignard reagents. Electronically different and sterically demanding aryl bromides including functionalized substrates and heteroaryl bromides are successfully cyanated in good to excellent yields. The efficiency of the present methodology is shown by the expeditious syntheses of interesting pharmaceutical intermediates. Notably, chemoselective monocyanation of dibromoarenes is also achieved.

Original languageEnglish
Pages (from-to)4217-4222
Number of pages6
JournalChemistry - A European Journal
Volume17
Issue number15
DOIs
StatePublished - 4 Apr 2011
Externally publishedYes

Keywords

  • Grignard reagents
  • N-CN reagents
  • aryl halides
  • benzonitriles
  • electrophilic cyanation

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