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Electrochemical Oxidative Esterification of Thiophenols: Efficient Access to Sulfinic Esters.
Current Organic Synthesis ( IF 1.8 ) Pub Date : 2020-10-31 , DOI: 10.2174/1570179417666200620215704
Chun-Hui Yang 1 , Cheng Wu 1 , Jun-Ming Zhang 1 , Xiang-Zhang Tao 1 , Jun Xu 1 , Jian-Jun Dai 1 , Hua-Jian Xu 1
Affiliation  

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.



中文翻译:

硫酚的电化学氧化酯化:有效获得亚硫酯。

背景:亚磺酸酯是有机合成中重要且有用的组成部分。

目的:本研究的目的是开发一种简单有效的亚磺酸酯合成方法。

材料和方法:选择从硫醇和醇进行恒流电解作为亚磺酸酯的合成方法。

结果与讨论:开发了一种新的电化学方法,由苯酚和醇类合成亚磺酸酯。使用目前的方法已经合成了多达27个亚磺酸酯的实例。该协议显示了良好的功能组耐受性以及高效率。此外,该协议可以轻松高效地按比例放大。值得注意的是,含杂环的底物,包括吡啶,噻吩和苯并噻唑,以良好的收率得到了所需的产物。提出了合理的反应机理。

结论:本研究不仅为合成亚磺酸酯提供了一种绿色高效的方法,而且还展示了电化学在有机合成中的新应用。人们认为,这种用于制备亚磺酸酯的绿色高效合成方案在将来将具有良好的应用。

更新日期:2020-10-30
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