Synthesis 2023; 55(18): 2959-2968
DOI: 10.1055/a-1996-8054
paper
Special Issue Electrochemical Organic Synthesis

Electrochemical Synthesis of 3-Sulfonylindoles via Annulation of o-Alkynylanilines with Sodium Sulfinates

Authors

  • Ping Jiang

    a   Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, P. R. of China
  • Rui Liu

    a   Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, P. R. of China
  • Xiangtai Meng

    a   Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, P. R. of China
    b   Sinopec Maoming Petrochemical Company, Maoming 525000, P. R. of China
  • Binnan Zheng

    c   Ningxia Best Pharmaceutical Chemical Co., Ltd., Yinchuan 750411, P. R. of China
  • Yu Zheng

    a   Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, P. R. of China
  • Shenlin Huang

    a   Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Nanjing Forestry University, Nanjing 210037, P. R. of China

Financial support provided by the Natural Science Foundation of China (32171724) and Jiangsu (BK20210607) is warmly acknowledged.


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Abstract

An electrochemical method to synthesize 3-sulfonylindoles from o-alkynylanilines and sodium sulfinates is disclosed. Featuring external oxidant-free, transition metal-free, and mild conditions, this sustainable approach tolerates a wide range of functional groups. Mechanistic studies are presented, revealing that (E)-bis(sulfonyl)stilbenes appear to be the key intermediates in this transformation.

Supporting Information



Publikationsverlauf

Eingereicht: 27. Oktober 2022

Angenommen nach Revision: 12. Dezember 2022

Accepted Manuscript online:
12. Dezember 2022

Artikel online veröffentlicht:
10. Januar 2023

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