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Xie Y, Wu X, Li C, et al. Ruthenium(II)-Catalyzed Redox-Neutral [3+2] Annulation of Indoles with Internal Alkynes via C-H Bond Activation: Accessing a Pyrroloindolone Scaffold. J Org Chem. 2017;82(10):5263-5273doi: 10.1021/acs.joc.7b00575.
Xie, Y., Wu, X., Li, C., Wang, J., Li, J., & Liu, H. (2017). Ruthenium(II)-Catalyzed Redox-Neutral [3+2] Annulation of Indoles with Internal Alkynes via C-H Bond Activation: Accessing a Pyrroloindolone Scaffold. The Journal of organic chemistry, 82(10), 5263-5273. https://doi.org/10.1021/acs.joc.7b00575
Xie, Yanan, et al. "Ruthenium(II)-Catalyzed Redox-Neutral [3+2] Annulation of Indoles with Internal Alkynes via C-H Bond Activation: Accessing a Pyrroloindolone Scaffold." The Journal of organic chemistry vol. 82,10 (2017): 5263-5273. doi: https://doi.org/10.1021/acs.joc.7b00575
Xie Y, Wu X, Li C, Wang J, Li J, Liu H. Ruthenium(II)-Catalyzed Redox-Neutral [3+2] Annulation of Indoles with Internal Alkynes via C-H Bond Activation: Accessing a Pyrroloindolone Scaffold. J Org Chem. 2017 May 19;82(10):5263-5273. doi: 10.1021/acs.joc.7b00575. Epub 2017 May 02. PMID: 28421753.
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J Org Chem. 2017 May 19;82(10):5263-5273. doi: 10.1021/acs.joc.7b00575. Epub 2017 May 02.

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

The Journal of organic chemistry

Yanan Xie, Xiaowei Wu, Chunpu Li, Jiang Wang, Jian Li, Hong Liu

Affiliations

  1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
  2. State Key Laboratory of Drug Research, Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , 555 Zu Chong Zhi Road, Shanghai 201203, China.
  3. University of Chinese Academy of Sciences , No. 19A Yuquan Road, Beijing 100049, China.

PMID: 28421753 DOI: 10.1021/acs.joc.7b00575

Abstract

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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