4.8 Article

Direct Transformation of N,N-Dimethylformamide to -CN: Pd-Catalyzed Cyanation of Heteroarenes via C-H Functionalization

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 32, Pages 12374-12377

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja204063z

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Funding

  1. Peking University
  2. National Natural Science Foundation of China [20702002, 20872003]
  3. National Basic Research Program of China (973 Program) [2009CB825300]

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This paper describes the direct cyanation of indoles and benzofurans employing N,N-dimethylformamide (DMF) as both reagent and solvent. Isotopic labeling experiments indicated that both the N and the C of the cyano group derived from DMF. This transformation offers an alternative method for preparing aryl nitriles, though it is currently limited in scope to indoles and benzofurans.

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