电化学双氧化策略实现从硫醚到α-氯代亚砜的合成

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

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.

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.