{"title":"Stereocontrolled synthesis of heterocycles from unactivated alkynes by photoredox/nickel dual-catalyzed cyclization","authors":"Bo-Rong Leng, Feng Yang, Jin-Lian Bai, Yu-Wen Huang, Qing-Quan Liu, Ping Wei, De-Cai Wang, Yi-Long Zhu","doi":"10.1039/d4qo01627k","DOIUrl":null,"url":null,"abstract":"We introduce an innovative nickel/photoredox dual catalytic sulfonyl-arylation method for synthesizing heterocyclic compounds directly from unactivated alkynes and aryl iodides. This green chemistry approach sidesteps traditional Heck reactions, eliminating reliance on excess metal catalysts and reagents. The method ensures high chemical selectivity, curbing side reactions and facilitating the stereoselective 6-exo-dig cyclization. It simplifies the production of nitrogen- or oxygen-containing heterocyclics, such as 3,4-dihydroisoquinolin-1(2H)-ones, tetrahydroisoquinolines, and isochroman derivatives, with potential applications in medicinal chemistry. The dual catalytic system enhances reactivity with unactivated substrates, marking a significant step in synthetic chemistry.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-11-06","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/d4qo01627k","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
We introduce an innovative nickel/photoredox dual catalytic sulfonyl-arylation method for synthesizing heterocyclic compounds directly from unactivated alkynes and aryl iodides. This green chemistry approach sidesteps traditional Heck reactions, eliminating reliance on excess metal catalysts and reagents. The method ensures high chemical selectivity, curbing side reactions and facilitating the stereoselective 6-exo-dig cyclization. It simplifies the production of nitrogen- or oxygen-containing heterocyclics, such as 3,4-dihydroisoquinolin-1(2H)-ones, tetrahydroisoquinolines, and isochroman derivatives, with potential applications in medicinal chemistry. The dual catalytic system enhances reactivity with unactivated substrates, marking a significant step in synthetic chemistry.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
