Electrochemical oxidations of thioethers: Modulation of oxidation potential using a hydrogen bonding network

Shiwen Liu; Bocheng Chen; Yi Yang; Yuhao Yang; Qianjin Chen; Xiaojun Zeng; Bo Xu

Electrochemistry Communications (Dec 2019)

Electrochemical oxidations of thioethers: Modulation of oxidation potential using a hydrogen bonding network

Shiwen Liu,
Bocheng Chen,
Yi Yang,
Yuhao Yang,
Qianjin Chen,
Xiaojun Zeng,
Bo Xu

Affiliations

Shiwen Liu: College of Textiles and Clothing, Yancheng Institute of Technology, Yancheng 224051, China
Bocheng Chen: Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Yi Yang: Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Yuhao Yang: Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Qianjin Chen: Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China
Xiaojun Zeng: Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China; Corresponding authors.
Bo Xu: Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China; Corresponding authors.

Journal volume & issue: Vol. 109

Abstract

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A highly efficient chemo-selective electrochemical oxidation of thioethers to sulfoxides and sulfones was developed. The hydrogen bonding network generated from hexafluoro-2-propanol (HFIP) and acetic acid (AcOH) plays an important role in the modulation of oxidation potential. The hydrogen bonding network complexes strongly with the sulfoxide, making it less prone to further oxidation. Therefore, thioethers can be selectively electrochemically oxidized to sulfoxides and over-oxidization could be minimized. Moreover, this modulation of oxidization via hydrogen bonding was supported by density functional theory (DFT) calculations and cyclic voltammetry experiments. Keywords: Hydrogen bonding network, Electrochemical oxidation, Sulfoxides and sulfones, Thioethers

Published in Electrochemistry Communications

ISSN: 1388-2481 (Print); 1873-1902 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Technology: Chemical technology: Industrial electrochemistry; Science: Chemistry
Website: https://www.journals.elsevier.com/electrochemistry-communications

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