Synthesis 2019; 51(18): 3511-3519
DOI: 10.1055/s-0037-1611888
paper
© Georg Thieme Verlag Stuttgart · New York

KI-Promoted Oxidative Coupling of Styrenes with Indoles under Metal-Free Conditions: Facile Access to C-3 Dicarbonyl Indoles

Authors

  • Bochao Zhou

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
  • Shiyu Guo

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
  • Zheng Fang

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
  • Zhao Yang

    b   School of Engineering, China Pharmaceutical University, No. 639 Longmian Avenue, Nanjing 211198, P. R. of China
  • Chengkou Liu

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
  • Wei He

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
  • Ning Zhu

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
  • Xin Li

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
  • Kai Guo

    a   College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China
    c   State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, 30 Puzhu Rd S., Nanjing 211816, P. R. of China   eMail: guok@njtech.edu.cn

This research was supported by the National Key Research and Development Program of China (2016YFB0301501), the National Natural Science Foundation of China (Grant Nos. 21776130 & 21878145), the Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture (Nos. X1821 & X1802), the Top-notch Academic Programs Project of Jiangsu Higher Education Institutions (TAPP), and the Postgraduate Research & Practice Innovation Program of Jiangsu Province.
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Publikationsverlauf

Received: 13. Mai 2019

Accepted after revision: 21. Juni 2019

Publikationsdatum:
11. Juli 2019 (online)


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Abstract

A new and efficient method for the synthesis of C-3 dicarbonyl indoles via oxidative cross-coupling of styrenes with indoles under metal-free conditions has been developed. Moreover, a broad scope of C-3 dicarbonyl indoles in moderate to good yields were obtained, and a plausible mechanism is proposed based on control and isotope-labeling experiments.

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