4.7 Article

Ruthenium(II)-Catalyzed Redox-Neutral [3+2] Annulation of Indoles with Internal Alkynes via C-H Bond Activation: Accessing a Pyrroloindolone Scaffold

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JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 10, 页码 5263-5273

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00575

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资金

  1. National Natural Science Foundation of China [81620108027, 21632008, 91229204, 81220108025]
  2. Chinese National Programs for Fundamental Research and Development [2015CB910304]
  3. National S&T Major Projects [2014ZX09507002-001]

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Ru(II)-catalyzed redox-neutral [3+2] annulation reactions of N-ethoxycarbamoyl indoles and internal alkynes via C-H bond activation are reported. This method features a broad internal alkyne scope, including various aryl/alkyl-, alkyl/alkyl-, and diaryl-substituted alkynes, good to excellent regioselectivity, diverse functional group tolerance, and mild reaction conditions. The N-ethoxycarbamoyl directing group, temperature, CsOAc, and ruthenium catalyst proved to be crucial for conversion and high regioselectivity. Additionally, preliminary mechanistic experiments were conducted, and a possible mechanism was proposed.

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