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Jia KY, Yu JB, Jiang ZJ, et al. Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism. J Org Chem. 2016;81(14):6049-55doi: 10.1021/acs.joc.6b01138.
Jia, K. Y., Yu, J. B., Jiang, Z. J., & Su, W. K. (2016). Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism. The Journal of organic chemistry, 81(14), 6049-55. https://doi.org/10.1021/acs.joc.6b01138
Jia, Kan-Yan, et al. "Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism." The Journal of organic chemistry vol. 81,14 (2016): 6049-55. doi: https://doi.org/10.1021/acs.joc.6b01138
Jia KY, Yu JB, Jiang ZJ, Su WK. Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism. J Org Chem. 2016 Jul 15;81(14):6049-55. doi: 10.1021/acs.joc.6b01138. Epub 2016 Jul 06. PMID: 27328874.
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J Org Chem. 2016 Jul 15;81(14):6049-55. doi: 10.1021/acs.joc.6b01138. Epub 2016 Jul 06.

Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism.

The Journal of organic chemistry

Kan-Yan Jia, Jing-Bo Yu, Zhi-Jiang Jiang, Wei-Ke Su

Affiliations

  1. Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology , Hangzhou 310014, People's Republic of China.
  2. National Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology , Hangzhou 310014, People's Republic of China.

PMID: 27328874 DOI: 10.1021/acs.joc.6b01138

Abstract

Construction of 3-vinylindoles (3) and β,β-diindolyl propionates (4) through solvent-free C-H functionalization has been explored under high-speed ball-milling conditions. The reaction selectivity is influenced by the catalyst dramatically: Pd(OAc)2 provides 3 in moderate to good yields, whereas PdX2 (X = Cl, I) affords 4 as the major products. The reaction mechanism has been further studied by using electrospray ionization mass spectrometry, implicating the dimeric palladium complex A as the key intermediate in an explanation of the selectivity.

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