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

Ping Jiang; Rui Liu; Xiangtai Meng; Binnan Zheng; Yu Zheng; Shenlin Huang

doi:10.1055/a-1996-8054

Synthesis, Table of Contents

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

^aJiangsu 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

^aJiangsu 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

^aJiangsu 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

^bSinopec Maoming Petrochemical Company, Maoming 525000, P. R. of China

,

Binnan Zheng

^cNingxia Best Pharmaceutical Chemical Co., Ltd., Yinchuan 750411, P. R. of China

,

Yu Zheng

^aJiangsu 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 ∗

^aJiangsu 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 Affiliations

Abstract

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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

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References

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