Dailin Zhuang, Le Cheng, Yichuan Yan, Yuting Tang, Zhenyang Wan, Jiahao Gu, Yuhong Lu, Xinyao Li and Ziyuan Li
{"title":"通过远程活化策略(RASE)多米诺活化烷基醚中的两个 C(sp3)-O 键的三组分官能团复分解反应","authors":"Dailin Zhuang, Le Cheng, Yichuan Yan, Yuting Tang, Zhenyang Wan, Jiahao Gu, Yuhong Lu, Xinyao Li and Ziyuan Li","doi":"10.1039/D4QO00740A","DOIUrl":null,"url":null,"abstract":"<p >A remote activating strategy enabled (RASE) three-component formal metathesis among an alkyl benzyl ether, an alkyl aryl ether and a Brønsted acid is achieved through metal-free domino activation of two C(sp<small><sup>3</sup></small>)–O bonds in alkyl ethers under mild conditions, leading to dealkoxylative C(sp<small><sup>3</sup></small>)–N coupling products in good to excellent yields. With the use of <em>in situ</em> generated benzyl alkyl ether in this smooth metathesis, this chemistry offers an efficient strategy for direct site-selective introduction of pharmaceutically significant monocyclic thiazol-2(3<em>H</em>)-one scaffolds onto specific benzylic sites. A probable mechanism is also provided based on the results of control experiments and DFT calculations.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":null,"pages":null},"PeriodicalIF":4.6000,"publicationDate":"2024-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Three-component formal metathesis via remote activating strategy enabled (RASE) domino activation of two C(sp3)–O bonds in alkyl ethers†\",\"authors\":\"Dailin Zhuang, Le Cheng, Yichuan Yan, Yuting Tang, Zhenyang Wan, Jiahao Gu, Yuhong Lu, Xinyao Li and Ziyuan Li\",\"doi\":\"10.1039/D4QO00740A\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A remote activating strategy enabled (RASE) three-component formal metathesis among an alkyl benzyl ether, an alkyl aryl ether and a Brønsted acid is achieved through metal-free domino activation of two C(sp<small><sup>3</sup></small>)–O bonds in alkyl ethers under mild conditions, leading to dealkoxylative C(sp<small><sup>3</sup></small>)–N coupling products in good to excellent yields. With the use of <em>in situ</em> generated benzyl alkyl ether in this smooth metathesis, this chemistry offers an efficient strategy for direct site-selective introduction of pharmaceutically significant monocyclic thiazol-2(3<em>H</em>)-one scaffolds onto specific benzylic sites. A probable mechanism is also provided based on the results of control experiments and DFT calculations.</p>\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.6000,\"publicationDate\":\"2024-06-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00740a\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00740a","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Three-component formal metathesis via remote activating strategy enabled (RASE) domino activation of two C(sp3)–O bonds in alkyl ethers†
A remote activating strategy enabled (RASE) three-component formal metathesis among an alkyl benzyl ether, an alkyl aryl ether and a Brønsted acid is achieved through metal-free domino activation of two C(sp3)–O bonds in alkyl ethers under mild conditions, leading to dealkoxylative C(sp3)–N coupling products in good to excellent yields. With the use of in situ generated benzyl alkyl ether in this smooth metathesis, this chemistry offers an efficient strategy for direct site-selective introduction of pharmaceutically significant monocyclic thiazol-2(3H)-one scaffolds onto specific benzylic sites. A probable mechanism is also provided based on the results of control experiments and DFT calculations.
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.