Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl2 and dimethyl/diethyl sulfoxides

Jingran Zhang; Beibei Zhang; Jiaxin He; Haofeng Shi; Yunfei Du

doi:10.1039/D2OB01580C

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Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl₂ and dimethyl/diethyl sulfoxides†

Jingran Zhang,^a Beibei Zhang,^a Jiaxin He,^a Haofeng Shi^a and Yunfei Du

*^a

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* Corresponding authors

^a School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China
E-mail: duyunfeier@tju.edu.cn

Abstract

A metal-free divergent synthesis of indole compounds dependent on a reagent via intramolecular C(sp²)–H amination was described. The reaction of 2-vinylanilines with DMSO/SOCl₂ at 70 °C was found to give 2-thiomethylindoles, while replacing DMSO with diethyl sulfoxide afforded 2-unsubstituted indoles in a highly selective manner.

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Article information

DOI: https://doi.org/10.1039/D2OB01580C
Article type: Communication
Submitted: 31 Aug 2022
Accepted: 21 Sep 2022
First published: 23 Sep 2022

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Org. Biomol. Chem., 2022,20, 7886-7890

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Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl₂ and dimethyl/diethyl sulfoxides

J. Zhang, B. Zhang, J. He, H. Shi and Y. Du, Org. Biomol. Chem., 2022, 20, 7886 DOI: 10.1039/D2OB01580C

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Organic & Biomolecular Chemistry