Direct intramolecular C(sp3)–H bond sulfonamidation to synthesize benzosultam derivatives under metal-free conditions

He Zhang; Meng-Chan Sun; Li-Ming Yin; Donghui Wei; Mao-Ping Song; Dandan Yang; Jun-Long Niu

doi:10.1039/D1QO01235E

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Direct intramolecular C(sp³)–H bond sulfonamidation to synthesize benzosultam derivatives under metal-free conditions†

He Zhang,^a Meng-Chan Sun,^a Li-Ming Yin,^a Donghui Wei,

*^a Mao-Ping Song,

*^a Dandan Yang

^a and Jun-Long Niu

*^a

Author affiliations

* Corresponding authors

^a Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China
E-mail: donghuiwei@zzu.edu.cn, mpsong@zzu.edu.cn, niujunlong@zzu.edu.cn

Abstract

Direct C(sp³)–H bond amination has become a hot topic due to its high efficiency in converting the C(sp³)–H bond to the C–N bond. Herein, we report an efficient intramolecular C(sp³)–H bond sulfonamidation under metal-free conditions, which provides a straightforward method for the synthesis of 5-membered cyclic sulfonamides (benzosultams). This protocol avoids the use of metal catalysts, oxidants, and any additives. Mechanistic experiments and DFT calculations revealed that the reaction proceeds through a proton transfer coupled with the S_N2 (PTS_N2) process, which is different from other pathways.

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Article information

DOI: https://doi.org/10.1039/D1QO01235E
Article type: Research Article
Submitted: 19 Aug 2021
Accepted: 20 Oct 2021
First published: 22 Oct 2021

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Org. Chem. Front., 2021,8, 6888-6894

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Direct intramolecular C(sp³)–H bond sulfonamidation to synthesize benzosultam derivatives under metal-free conditions

H. Zhang, M. Sun, L. Yin, D. Wei, M. Song, D. Yang and J. Niu, Org. Chem. Front., 2021, 8, 6888 DOI: 10.1039/D1QO01235E

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