Electrochemical Oxidative Cross-Coupling Reactions of Ketene Dithioacetals and Dichalcogenides to Construct C−Se/C−S Bonds

A green protocol for construction of C−Se bonds from ketene dithioacetals and diselenides through direct electrochemical oxidative cross-coupling has been developed. This reaction was carried out in an undivided cell system with NaBF 4 as the electrolyte and CH 3 CN as the solvent through galvanosta...

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Bibliographic Details
Published in:Journal of the Electrochemical Society 2024-05, Vol.171 (5), p.55501
Main Authors: Wang, Jiaxu, Liu, Xin, Feng, Chenglong, Sun, Qing, She, Yuanbin, Shen, Zhenlu, Li, Meichao
Format: Article
Language:English
Subjects:
dichalcogenides
electrosynthesis
organic electrochemistry
oxidative cross-coupling
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Summary:A green protocol for construction of C−Se bonds from ketene dithioacetals and diselenides through direct electrochemical oxidative cross-coupling has been developed. This reaction was carried out in an undivided cell system with NaBF 4 as the electrolyte and CH 3 CN as the solvent through galvanostatic electrolysis. A series of substituted ketene dithioacetals and diselenides were tolerant and the desired tetrasubstituted alkenyl selenides were obtained in moderate to excellent yields. In addition, construction of C−S bond from ketene dithioacetals and disulfides through electrochemical method in the presence of KI was also successfully realized. It exhibited high efficiency and broad functional group tolerance.
ISSN:0013-4651
1945-7111
DOI:10.1149/1945-7111/ad40d3