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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

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
› Author AffiliationsFinancial 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.

Key words

organic electrochemistry - indoles - 3-sulfonylindoles - oxidation - sodium sulfinates - alkynylanilines

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1996-8054.
  • Supporting Information


Publication History

Received: 27 October 2022

Accepted after revision: 12 December 2022

Accepted Manuscript online:
12 December 2022

Article published online:
10 January 2023

© 2022. Thieme. All rights reserved

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