Mechanism of Pd-catalysed C(sp3)–H arylation of thioethers with Ag(I) additives

Wenjing Liu; Zheyuan Liu; Xiaowei Liu; Yanfeng Dang

doi:10.1039/D1OB00704A

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Mechanism of Pd-catalysed C(sp³)–H arylation of thioethers with Ag(i) additives†

Wenjing Liu,

^a Zheyuan Liu,^b Xiaowei Liu*^a and Yanfeng Dang

*^b

Author affiliations

* Corresponding authors

^a Key Laboratory for Environmental Factors Control of Agro-product Quality Safety, Agro-Environmental Protection Institute, Ministry of Agriculture and Rural Affairs, Tianjin 300191, China
E-mail: xwliu2006@163.com

^b Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, Tianjin University, Tianjin 300072, China
E-mail: yanfeng.dang@tju.edu.cn

Abstract

Mechanistic studies reveal that Pd-catalyzed C(sp³)–H arylation of thioethers with silver(I) additives takes place via C(sp³)–H activation, oxidative addition and reductive elimination, wherein all steps proceed via the heterodimeric Pd–Ag pathway. Besides, the active heterodimeric Pd–Ag species are detected by mass spectrometry via control experiments.

This article is part of the themed collection: Mechanistic, computational & physical organic chemistry in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB00704A
Article type: Communication
Submitted: 11 Apr 2021
Accepted: 14 Jul 2021
First published: 14 Jul 2021

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Org. Biomol. Chem., 2021,19, 6766-6770

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Mechanism of Pd-catalysed C(sp³)–H arylation of thioethers with Ag(I) additives

W. Liu, Z. Liu, X. Liu and Y. Dang, Org. Biomol. Chem., 2021, 19, 6766 DOI: 10.1039/D1OB00704A

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Organic & Biomolecular Chemistry