Chengkan Gao , Lin Li , Xiangyang Lin , Renming Pan , Wenfang Zheng
{"title":"选择性氟介导的氧化脱胺:芳香醛合成的可扩展方法","authors":"Chengkan Gao , Lin Li , Xiangyang Lin , Renming Pan , Wenfang Zheng","doi":"10.1080/00397911.2025.2458625","DOIUrl":null,"url":null,"abstract":"<div><div>The catalyst-free oxidative deamination without over-oxidation constitutes a considerable challenge in the synthesis of aromatic aldehydes. Herein, we introduce a Selectfluor-mediated Lewis acid system that achieves the oxidative deamination of benzylic amines with α-C-H bond activation to yield aromatic aldehydes. Noteworthy features include the direct use of Selectfluor that can activate the α-C-H bond under catalyst- and base-free conditions via the in-situ dehydrofluorination effect. The approach is demonstrated for a broad scope of benzylic amines without over-oxidation and accomplishes 200 mmol scale synthesis.</div></div>","PeriodicalId":22119,"journal":{"name":"Synthetic Communications","volume":"55 5","pages":"Pages 433-441"},"PeriodicalIF":1.8000,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Selectfluor-mediated oxidative deamination: A scalable approach to aromatic aldehydes synthesis\",\"authors\":\"Chengkan Gao , Lin Li , Xiangyang Lin , Renming Pan , Wenfang Zheng\",\"doi\":\"10.1080/00397911.2025.2458625\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The catalyst-free oxidative deamination without over-oxidation constitutes a considerable challenge in the synthesis of aromatic aldehydes. Herein, we introduce a Selectfluor-mediated Lewis acid system that achieves the oxidative deamination of benzylic amines with α-C-H bond activation to yield aromatic aldehydes. Noteworthy features include the direct use of Selectfluor that can activate the α-C-H bond under catalyst- and base-free conditions via the in-situ dehydrofluorination effect. The approach is demonstrated for a broad scope of benzylic amines without over-oxidation and accomplishes 200 mmol scale synthesis.</div></div>\",\"PeriodicalId\":22119,\"journal\":{\"name\":\"Synthetic Communications\",\"volume\":\"55 5\",\"pages\":\"Pages 433-441\"},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2025-01-31\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthetic Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S003979112500013X\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthetic Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S003979112500013X","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Selectfluor-mediated oxidative deamination: A scalable approach to aromatic aldehydes synthesis
The catalyst-free oxidative deamination without over-oxidation constitutes a considerable challenge in the synthesis of aromatic aldehydes. Herein, we introduce a Selectfluor-mediated Lewis acid system that achieves the oxidative deamination of benzylic amines with α-C-H bond activation to yield aromatic aldehydes. Noteworthy features include the direct use of Selectfluor that can activate the α-C-H bond under catalyst- and base-free conditions via the in-situ dehydrofluorination effect. The approach is demonstrated for a broad scope of benzylic amines without over-oxidation and accomplishes 200 mmol scale synthesis.
期刊介绍:
Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.