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Electrochemical dual-oxidation strategy enables access to α-chlorosulfoxides from sulfides
Science Bulletin ( IF 18.9 ) Pub Date : 2021-07-03 , DOI: 10.1016/j.scib.2021.07.004
Huamin Wang 1 , Mingming Yu 1 , Panyue Zhang 1 , Hao Wan 2 , Hengjiang Cong 1 , Aiwen Lei 3
Affiliation  

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 to α-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.



中文翻译:

电化学双氧化策略能够从硫化物中获得α-氯亚砜

电化学为分子制造提供了强大的工具,通过实现创新的反应途径解决了合成化学中棘手的挑战。在此,双功能试剂盐酸水溶液被用于建立电化学选择性双氧化方法,该方法可以从硫化物中获得 α-氯亚砜。该策略具有广泛的底物范围、高非对映选择性和区域选择性。氨基酸和药物衍生物的后期修饰进一步凸显了实用性。此外,详细的机理研究表明,这种选择性化学转化的关键成功在于阳极的双重氧化过程。这种电化学双氧化策略可能具有广泛的普适性;

更新日期:2021-07-03
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