4.6 Article

A Novel and Convenient Synthesis of Benzonitriles: Electrophilic Cyanation of Aryl and Heteroaryl Bromides

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 15, 页码 4217-4222

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201003388

关键词

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

资金

  1. Alexander-von-Humboldt-Stiftung
  2. State of Mecklenburg-Western Pomerania
  3. BMBF
  4. DFG (Leibniz Prize)

向作者/读者索取更多资源

N-Cyano-N-phenyl-p-methyl-benzenesulfonamide 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.

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