Jidan Liu , Ruilian Liang , Qinglian Yan , Liyao Zheng , Zhao-Qing Liu , Shouzhi Pu
{"title":"Recent advances in the synthesis of nitrogen heterocycles via Rh(iii)-catalyzed chelation-assisted C–H activation/annulation with diazo compounds","authors":"Jidan Liu , Ruilian Liang , Qinglian Yan , Liyao Zheng , Zhao-Qing Liu , Shouzhi Pu","doi":"10.1039/d5qo00111k","DOIUrl":null,"url":null,"abstract":"<div><div>Diazo compounds are a class of readily available and versatile reagents in modern organic synthesis that have been used as valuable synthetic building blocks for a diverse range of important organic transformations due to their convenient preparation and high reactivity. In this review, the advancements in the synthesis of nitrogen-containing heterocycles <em>via</em> Rh(<span>iii</span>)-catalyzed chelation-assisted tandem C–H activation/carbene insertion/annulation with diazo compounds as carbene precursors have been summarized. A variety of structurally diverse nitrogen heterocyclic scaffolds, such as indoles, isoindolones, carbazoles, isoquinolines, isoquinolones, 2<em>H</em>-indazoles, indazolones, cinnolines, 2,3-benzodiazepines, azepines, and diazepinones can be easily prepared from different diazo compounds in a highly efficient and environmentally benign manner.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 9","pages":"Pages 3065-3106"},"PeriodicalIF":0.0000,"publicationDate":"2025-02-27","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/S2052412925001470","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/2/17 0:00:00","PubModel":"Epub","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Diazo compounds are a class of readily available and versatile reagents in modern organic synthesis that have been used as valuable synthetic building blocks for a diverse range of important organic transformations due to their convenient preparation and high reactivity. In this review, the advancements in the synthesis of nitrogen-containing heterocycles via Rh(iii)-catalyzed chelation-assisted tandem C–H activation/carbene insertion/annulation with diazo compounds as carbene precursors have been summarized. A variety of structurally diverse nitrogen heterocyclic scaffolds, such as indoles, isoindolones, carbazoles, isoquinolines, isoquinolones, 2H-indazoles, indazolones, cinnolines, 2,3-benzodiazepines, azepines, and diazepinones can be easily prepared from different diazo compounds in a highly efficient and environmentally benign manner.