{"title":"Photo- and Copper-Catalyzed Enantioselective Oxidation of Benzylic C(sp3)–H Bonds","authors":"Fu Li, Xian-Ming Liu, Jia-Bin Pan, Ling Dai, Yin Yang, Li-Jun Xiao, Chao Fan, Qi-Lin Zhou","doi":"10.1021/jacs.5c04142","DOIUrl":null,"url":null,"abstract":"Here, we report a photo- and copper-catalyzed enantioselective oxidation of benzylic C(sp<sup>3</sup>)–H bonds using <i>N</i>-hydroxyphthalimide as the oxygenated reagent. The reaction proceeds under mild conditions and does not require excess substrates or oxidants. The oxidation products can be readily transformed into chiral benzylic alcohols or hydroxylamines. Preliminary mechanism studies suggest that the oxidation reaction proceeds via a free radical mechanism.","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":"51 1","pages":""},"PeriodicalIF":14.4000,"publicationDate":"2025-05-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/jacs.5c04142","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Here, we report a photo- and copper-catalyzed enantioselective oxidation of benzylic C(sp3)–H bonds using N-hydroxyphthalimide as the oxygenated reagent. The reaction proceeds under mild conditions and does not require excess substrates or oxidants. The oxidation products can be readily transformed into chiral benzylic alcohols or hydroxylamines. Preliminary mechanism studies suggest that the oxidation reaction proceeds via a free radical mechanism.
期刊介绍:
The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.