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

Autor: Shiwen Liu, Bocheng Chen, Yi Yang, Yuhao Yang, Qianjin Chen, Xiaojun Zeng, Bo Xu
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: Electrochemistry Communications, Vol 109, Iss , Pp - (2019)
Druh dokumentu: article
ISSN: 1388-2481
DOI: 10.1016/j.elecom.2019.106583
Popis: 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
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