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Synlett 2018; 29(14): 1914-1920
DOI: 10.1055/s-0037-1610532
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Sulfenylindoles from Indoles and Various Sulfenylation Agents through Aerobic Oxidative C–S Bond Coupling

Chaorong Xu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Shanli Yi
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Meichao Li*
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Xinquan Hu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Nan Sun
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Liqun Jin
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Baoxiang Hu
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
,
Zhenlu Shen*
College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, P. R. of China   Email: limc@zjut.edu.cn   Email: zhenlushen@zjut.edu.cn
› Author AffiliationsThis project was supported by the National Natural Science Foundation of China (21776260, 21773211 and 21376224) and the Natural Science Foundation of Zhejiang Province (LY17B060007).
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Publication History

Received: 02 June 2018

Accepted after revision: 02 July 2018

Publication Date:
02 August 2018 (online)

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Abstract

A novel aerobic catalytic oxidation system for the sulfenylation of indoles with a variety of sulfenylation agents through oxidative C–S bond coupling has been successfully developed. The reactions were performed with potassium iodide as the catalyst, sodium nitrite as the co-catalyst, and molecular oxygen as the terminal oxidant in the presence of acetic acid. Under the optimal reaction conditions, a number of indoles could be sulfenylated with Bunte salts, thiols, or disulfides to generate 3-sulfenylindoles in good yields. This protocol provided an efficient and environmentally benign strategy for the synthesis of 3-sulfenylindoles.

Key words

indoles - sulfenylation - C–S bond coupling - catalytic oxidation - regioselectivity

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610532.
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