Electrochemical dual-oxidation strategy enables access toα-chlorosulfoxides from sulfides  

电化学双氧化策略实现从硫醚到α-氯代亚砜的合成

作　　者：Huamin Wang Mingming Yu Panyue Zhang Hao Wan Hengjiang Cong Aiwen Lei 王华敏;余明明;张盘月;万好;丛恒将;雷爱文(The Institute for Advanced Studies(IAS),College of Chemistry and Molecular Sciences,Wuhan University,Wuhan 430072,China;Department of Chemical and Materials Engineering,King Abdulaziz University,Jeddah 21589,Saudi Arabia;National Research Center for Carbohydrate Synthesis,Jiangxi Normal University,Nanchang 330022,China)

机构地区：[1]The Institute for Advanced Studies(IAS),College of Chemistry and Molecular Sciences,Wuhan University,Wuhan 430072,China [2]Department of Chemical and Materials Engineering,King Abdulaziz University,Jeddah 21589,Saudi Arabia [3]National Research Center for Carbohydrate Synthesis,Jiangxi Normal University,Nanchang 330022,China

出　　处：《Science Bulletin》2022年第1期79-84,M0004,共7页科学通报（英文版）

基　　金：supported by the National Natural Science Foundation of China(22031008);Science Foundation of Wuhan(2020010601012192);The Program of Introducing Talents of Discipline to Universities of China(111 Program)is also appreciated。

摘　　要：Electrochemistry contributes a strong tool for the manufacture of molecules,addressing intractable challenges in synthetic chemistry by enabling innovative reaction pathways.Herein,a bifunctional reagent,aqueous hydrochloric acid,is used to establish an electrochemical selective dual-oxidation approach that gives access toα-chlorosulfoxides from sulfides.This strategy presents broad substrate scope,high diastereoselectivity,and regioselectivity.The late-stage modification of amino acids and pharmaceutical derivatives further highlights the utility.Furthermore,detailed mechanistic studies reveal that the key success for this selective chemical transformation is the dual-oxidation process at the anode.This electrochemical dual-oxidation strategy may have wide universality;we anticipate diverse applications of this protocol across the many fields of chemistry.电化学通过发展新的反应途径解决了合成化学中棘手的挑战,为分子的构建提供了一个强大的工具.本文发展了一种电化学选择性双氧化策略,以盐酸为双功能化试剂实现了从硫醚合成α-氯代亚砜.该策略底物范围广、具有高非对映选择性和区域选择性.重要的是,对氨基酸和药物衍生物的后期修饰进一步突出了该策略的实用性.此外,机理研究表明,阳极的双氧化过程是该选择性转化成功的关键.这种电化学双氧化策略可能具有广谱性,预计该策略在许多化学领域具有广泛应用.

关 键 词：Dual-oxidation DIASTEREOSELECTIVITY Sulfur-containing compounds ELECTROCHEMISTRY Regioselectivity 

分 类 号：O621.25[理学—有机化学]