4.7 Article

Weak Coordinating Carbonyl-Directed Rhodium(III)-Catalyzed C-H Activation at the C4-Position of Indole with Allyl Alcohols

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 8, Pages 5516-5524

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00277

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Funding

  1. SERB,New-Delhi [EMR/2016/006358]
  2. Indian Institute of Science
  3. R. L. Fine Chem

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A weakly coordinating carbonyl-directed coupling of allyl alcohols at the C-4 position of indole derivatives under the C-H activation conditions catalyzed by Rh(III) is reported. This results in alkylation at the C-4 position of indole derivatives exclusively. The obtained product forms a tricyclic derivative under aldol reaction conditions, which can be a potential precursor for synthesizing a few alkaloid molecules such as ergot, hapalindole alkaloids, and related heterocyclic compounds.

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