4.8 Article

Synthesis of 3-Acylindoles by Palladium-Catalyzed Acylation of Free (N-H) Indoles with Nitriles

Journal

ORGANIC LETTERS
Volume 15, Issue 4, Pages 788-791

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol303440y

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Funding

  1. NSFC [91021004]
  2. National Basic Research Program of China [2011CB921402]
  3. Key Project of Science and Technology of the Department of Education, Anhui Province, China [KJ2010ZD05]

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An efficient palladium-catalyzed synthesis of 3-acylindoles using free (N-H) indoles and nitrites 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 nitrites and subsequent hydrolysis of ketimines Is proposed.

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