4.8 Article

Ir(I)-Catalyzed C-H Bond Alkylation of C2-Position of Indole with Alkenes: Selective Synthesis of Linear or Branched 2-Alkylindoles

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 42, Pages 17474-17477

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja308742x

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Funding

  1. Molecular Activation Directed toward Straightforward Synthesis, MEXT, Japan
  2. Global COE program Practical Chemical Wisdom, Waseda University, Japan

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A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.

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