Yuxin Pan, Kaikai Qiao, Bing-ru Shao, Xin Du, Wen-feng Jiang, Lei Shi
{"title":"FeCl3 catalyzed direct oxime etherification of inert C(sp3)-H via photo-driven HAT in batch and continuous flow mode","authors":"Yuxin Pan, Kaikai Qiao, Bing-ru Shao, Xin Du, Wen-feng Jiang, Lei Shi","doi":"10.1016/j.tetlet.2025.155769","DOIUrl":null,"url":null,"abstract":"<div><div>We report an efficient photocatalytic strategy for direct oxime etherification of unactivated C(sp<sup>3</sup>)-H bonds through hydrogen atom transfer (HAT) activation, employing low loading FeCl<sub>3</sub> as catalyst under blue light irradiation. This methodology demonstrates a broad substrates scope with excellent functional group tolerence, including cycloalkanes, ethers, amides, sulfonamides, phosphoramides, and ketones. Furthermore, the reaction system exhibits remarkable scalability through continuous flow photoreactor, achieving practical gram-scale production of pharmaceutically relevant oxime ether derivatives with improved yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155769"},"PeriodicalIF":1.5000,"publicationDate":"2025-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925003181","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We report an efficient photocatalytic strategy for direct oxime etherification of unactivated C(sp3)-H bonds through hydrogen atom transfer (HAT) activation, employing low loading FeCl3 as catalyst under blue light irradiation. This methodology demonstrates a broad substrates scope with excellent functional group tolerence, including cycloalkanes, ethers, amides, sulfonamides, phosphoramides, and ketones. Furthermore, the reaction system exhibits remarkable scalability through continuous flow photoreactor, achieving practical gram-scale production of pharmaceutically relevant oxime ether derivatives with improved yields.
期刊介绍:
Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.