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Issue 6, 2017
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I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

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Abstract

Readily available triethylammonium thiolates were proved to be new and eco-friendly sulfenylating agents for the efficient and practical construction of sulfenylated indoles and pyrroles (48 examples) with good to excellent yields under metal-free and microwave irradiation conditions. The combination of I2 and DMSO enabled direct C–S bond formation, allowing easy and low-cost access to new functionalized C,S-tethered bisindoles and pyrrole–indole pairs with a wide diversity of substituents. The mechanism involving S–S and S–I bond-forming/breaking events was proposed.

Graphical abstract: I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

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Publication details

The article was received on 24 Dec 2016, accepted on 16 Feb 2017 and first published on 20 Feb 2017


Article type: Research Article
DOI: 10.1039/C6QO00851H
Citation: Org. Chem. Front., 2017,4, 1091-1102
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    I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents

    W. Fan, Z. Yang, B. Jiang and G. Li, Org. Chem. Front., 2017, 4, 1091
    DOI: 10.1039/C6QO00851H

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