Ning Xian, Xiaochen Ji, Guo-Jun Deng, Huawen Huang
{"title":"Visible-Light-Induced photoredox aerobic coupling of sulfonium ylides and amines leading to E-selective formation of 2-amino-2-butene-1,4-diones","authors":"Ning Xian, Xiaochen Ji, Guo-Jun Deng, Huawen Huang","doi":"10.1039/d4qo02208d","DOIUrl":null,"url":null,"abstract":"A novel visible-light-induced photoredox three-component aerobic coupling reaction of sulfoxonium ylides and amines is reported. The protocol provides a general strategy for the construction of structurally valuable highly functionalized 2-amino-2-butene-1,4-dione scaffolds in a chemo- and regioselective manner. This methodology stands out for its mild conditions, no requirement of organic oxidants or other additives, and good E-selectivity. Mechanistic studies suggested that dioxygen serves as a dual functional reagent not only in photoredox cycle (light reaction) but the aerobic oxidative coupling (dark reaction).","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"71 1","pages":""},"PeriodicalIF":4.6000,"publicationDate":"2025-01-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d4qo02208d","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A novel visible-light-induced photoredox three-component aerobic coupling reaction of sulfoxonium ylides and amines is reported. The protocol provides a general strategy for the construction of structurally valuable highly functionalized 2-amino-2-butene-1,4-dione scaffolds in a chemo- and regioselective manner. This methodology stands out for its mild conditions, no requirement of organic oxidants or other additives, and good E-selectivity. Mechanistic studies suggested that dioxygen serves as a dual functional reagent not only in photoredox cycle (light reaction) but the aerobic oxidative coupling (dark reaction).
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.