{"title":"Enantioselective C–H amidation of sulfondiimines for the synthesis of 1,2,4-benzothiadiazine-1-imines under cobalt catalysis†","authors":"Ayami Murata, Tomonori Endo, Yuki Hirata, Kosuke Higashida, Tatsuhiko Yoshino and Shigeki Matsunaga","doi":"10.1039/D5QO00355E","DOIUrl":null,"url":null,"abstract":"<p >In comparison to the notable recent progress in the derivatization of sulfoximines <em>via</em> directed C–H activation, the C–H activation/functionalization of sulfondiimines is underdeveloped. Here, we report C–H amidation/cyclization reactions of sulfondiimines with dioxazolones catalyzed by the combination of a cobalt(<small>III</small>) catalyst and a pseudo <em>C</em><small><sub>2</sub></small>-symmetric chiral carboxylic acid, leading to the formation of unprecedented 1,2,4-benzothiadiazine-1-imine structures in high enantioselectivity.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 15","pages":" 4236-4241"},"PeriodicalIF":4.7000,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/qo/d5qo00355e?page=search","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2025/qo/d5qo00355e","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
In comparison to the notable recent progress in the derivatization of sulfoximines via directed C–H activation, the C–H activation/functionalization of sulfondiimines is underdeveloped. Here, we report C–H amidation/cyclization reactions of sulfondiimines with dioxazolones catalyzed by the combination of a cobalt(III) catalyst and a pseudo C2-symmetric chiral carboxylic acid, leading to the formation of unprecedented 1,2,4-benzothiadiazine-1-imine structures in high enantioselectivity.
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.