{"title":"Oxime-Ether Group Transfer to Unpolarized C(sp3)─H Bonds via Light-Induced HAT Catalysis.","authors":"Jayanta Dey, Nayan Banerjee, Joyram Guin","doi":"10.1002/asia.202500068","DOIUrl":null,"url":null,"abstract":"<p><p>In this study, we demonstrate an effective method for the direct conversion of alkane chemical feedstocks to valuable oxime-ethers through the functionalization of unpolarized C(sp<sup>3</sup>)─H bonds using light-induced HAT-catalysis. The process operates at room temperature, utilizing low catalyst loading (ppm level) and a reduced substrate-to-reagent ratio. Notably, the reaction can also be performed in sunlight, which makes the process further attractive toward sustainable synthesis of functionalized oxime-ethers. The process displays a broad substrate scope, rendering desired products with up to 90% yields. The reaction is shown to be scalable. Through a series of mechanistic control studies, a radical reaction pathway featuring HAT-induced C─H functionalization is implicated in the process.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e00068"},"PeriodicalIF":3.5000,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202500068","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
In this study, we demonstrate an effective method for the direct conversion of alkane chemical feedstocks to valuable oxime-ethers through the functionalization of unpolarized C(sp3)─H bonds using light-induced HAT-catalysis. The process operates at room temperature, utilizing low catalyst loading (ppm level) and a reduced substrate-to-reagent ratio. Notably, the reaction can also be performed in sunlight, which makes the process further attractive toward sustainable synthesis of functionalized oxime-ethers. The process displays a broad substrate scope, rendering desired products with up to 90% yields. The reaction is shown to be scalable. Through a series of mechanistic control studies, a radical reaction pathway featuring HAT-induced C─H functionalization is implicated in the process.
期刊介绍:
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).