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Current Organic Synthesis

Author(s): Chun-Hui Yang, Cheng Wu, Jun-Ming Zhang, Xiang-Zhang Tao, Jun Xu, Jian-Jun Dai* and Hua-Jian Xu*

DOI: 10.2174/1570179417666200620215704

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Electrochemical Oxidative Esterification of Thiophenols: Efficient Access to Sulfinic Esters

Page: [540 - 547] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

Background: The sulfinic esters are important and useful building blocks in organic synthesis.

Objective: The aim of this study was to develop a simple and efficient method for the synthesis of sulfinic esters.

Materials and Methods: Constant current electrolysis from thiols and alcohols was selected as the method for the synthesis of sulfinic esters.

Results and Discussion: A novel electrochemical method for the synthesis of sulfinic esters from thiophenols and alcohols has been developed. Up to 27 examples of sulfinic esters have been synthesized using the current methods. This protocol shows good functional group tolerance as well as high efficiency. In addition, this protocol can be easily scaled up with good efficiency. Notably, heterocycle-containing substrates, including pyridine, thiophene, and benzothiazole, gave the desired products in good yields. A plausible reaction mechanism is proposed.

Conclusion: This research not only provides a green and efficient method for the synthesis of sulfinic esters but also shows new applications of electrochemistry in organic synthesis. It is considered that this green and efficient synthetic protocol used to prepare sulfinic esters will have good applications in the future.

Keywords: Electrochemistry, free radical, green chemistry, oxidation, esterification, thiophenol.

Graphical Abstract

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