Hejun An , Zhi Cui , Jinchao Liang , Xingxing Ma , Jinglong Chen , Qiuling Song
{"title":"Fe-Catalyzed B–H and N–H insertion reactions of iodonium ylides†","authors":"Hejun An , Zhi Cui , Jinchao Liang , Xingxing Ma , Jinglong Chen , Qiuling Song","doi":"10.1039/d4qo01916d","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, B–H and N–H insertion reactions of iodonium ylides in the presence of an iron catalyst complexed with imidazo[1,5-<em>a</em>]pyridine are developed, achieving the borylation and amination of 1,3-dicarbonyl derivatives under mild reaction conditions. Mechanistic investigations show that an iron carbene is involved in this process. Besides, this reaction features high efficiency, a broad substrate scope and good functional group tolerance, and propionate ester scaffolds can be introduced into various drug molecules <em>via</em> this protocol.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4058-4065"},"PeriodicalIF":0.0000,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052412925002323","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, B–H and N–H insertion reactions of iodonium ylides in the presence of an iron catalyst complexed with imidazo[1,5-a]pyridine are developed, achieving the borylation and amination of 1,3-dicarbonyl derivatives under mild reaction conditions. Mechanistic investigations show that an iron carbene is involved in this process. Besides, this reaction features high efficiency, a broad substrate scope and good functional group tolerance, and propionate ester scaffolds can be introduced into various drug molecules via this protocol.