The C(sp3)–H bond functionalization of thioethers with styrenes with insight into the mechanism

Zhan Yan; Nai-Xing Wang; Lei-Yang Zhang; Yue-Hua Wu; Jian-Li Li; Meng-Yao She; Xue-Wang Gao; Ke Feng; Yalan Xing

doi:10.1039/D2OB00872F

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The C(sp³)–H bond functionalization of thioethers with styrenes with insight into the mechanism†

Zhan Yan,^ab Nai-Xing Wang,

*^a Lei-Yang Zhang,^a Yue-Hua Wu,^a Jian-Li Li,

*^b Meng-Yao She,^b Xue-Wang Gao,^a Ke Feng^a and Yalan Xing

*^c

Author affiliations

* Corresponding authors

^a Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, China
E-mail: nxwang@mail.ipc.ac.cn

^b College of Chemistry and Materials Science, Northwest University, Xi'an, China
E-mail: lijianli@nwu.edu.cn

^c Department of Chemistry, William Paterson University of New Jersey, New Jersey, USA
E-mail: xingy@wpunj.edu

Abstract

A metal-free inactive C(sp³)–H bond functionalization of thioethers with styrenes using TBHP as an initiator and DBU as a base has been developed. This transformation has broken through the low activity of thioethers and realized moderate yields. Herein extended experiments were conducted to confirm the radical relay process, reaction energy and intermediate transformations.

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Article information

DOI: https://doi.org/10.1039/D2OB00872F
Article type: Paper
Submitted: 07 May 2022
Accepted: 04 Jul 2022
First published: 18 Jul 2022

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Org. Biomol. Chem., 2022,20, 5845-5851

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The C(sp³)–H bond functionalization of thioethers with styrenes with insight into the mechanism

Z. Yan, N. Wang, L. Zhang, Y. Wu, J. Li, M. She, X. Gao, K. Feng and Y. Xing, Org. Biomol. Chem., 2022, 20, 5845 DOI: 10.1039/D2OB00872F

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Organic & Biomolecular Chemistry