Jorge García-Lacuna , Gema Domínguez , Ángel Manu Martínez , Javier Pérez-Castells
{"title":"Recent advances in hydrofunctionalisation of cyclopropenes via carbon–heteroatom bond formation","authors":"Jorge García-Lacuna , Gema Domínguez , Ángel Manu Martínez , Javier Pérez-Castells","doi":"10.1039/d4qo02441a","DOIUrl":null,"url":null,"abstract":"<div><div>Hydrofunctionalisation of cyclopropenes represents a redox-neutral and atom-economic strategy to obtain polyfunctionalised cyclopropanes. The extraordinary potential of heteroatom-containing cyclopropanes in organic and medicinal chemistry has driven a growing interest in developing new methodologies for the selective addition of hydrogen–heteroatom bonds across the carbon–carbon double bond of cyclopropenes. Despite the apparent simplicity of these transformations, they involve significant challenges in terms of stereoselectivity. Continuous efforts to control the regio-, diastereo- and enantioselectivity of these processes, especially by applying different transition metal catalysts, have led to numerous reports. This review comprehensively examines the developments and advances in the selective hydrofunctionalisation of cyclopropenes by carbon–heteroatom bond formation.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 7","pages":"Pages 2525-2551"},"PeriodicalIF":0.0000,"publicationDate":"2025-02-12","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/S2052412925000968","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
Hydrofunctionalisation of cyclopropenes represents a redox-neutral and atom-economic strategy to obtain polyfunctionalised cyclopropanes. The extraordinary potential of heteroatom-containing cyclopropanes in organic and medicinal chemistry has driven a growing interest in developing new methodologies for the selective addition of hydrogen–heteroatom bonds across the carbon–carbon double bond of cyclopropenes. Despite the apparent simplicity of these transformations, they involve significant challenges in terms of stereoselectivity. Continuous efforts to control the regio-, diastereo- and enantioselectivity of these processes, especially by applying different transition metal catalysts, have led to numerous reports. This review comprehensively examines the developments and advances in the selective hydrofunctionalisation of cyclopropenes by carbon–heteroatom bond formation.