{"title":"RaabPhos, an Air-Stable, Highly Active Ferrocenyl Phosphasilinane Ligand, for Palladium-Catalyzed C-C and C-N Bond-Forming Cross-Coupling Reactions.","authors":"Michael G Raab,Oliver Trapp,Dino Berthold","doi":"10.1021/acs.orglett.5c03832","DOIUrl":null,"url":null,"abstract":"The air-stable, highly active ferrocenyl phosphasilinane ligand RaabPhos has been synthesized in four steps from readily available starting materials. Although the ligand is not sterically overloaded, it is highly electron-rich and therefore the corresponding Pd catalyst of high activity. Furthermore, RaabPhos is air-stable as a solid as well as in solution. With the application of this novel ligand in various Pd-catalyzed C-C and C-N bond-forming cross-coupling reactions, its reactivity toward unreactive (hetero)aryl chlorides has been explored. We observed, in general, high yields in these transformations under mild conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"122 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c03832","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
The air-stable, highly active ferrocenyl phosphasilinane ligand RaabPhos has been synthesized in four steps from readily available starting materials. Although the ligand is not sterically overloaded, it is highly electron-rich and therefore the corresponding Pd catalyst of high activity. Furthermore, RaabPhos is air-stable as a solid as well as in solution. With the application of this novel ligand in various Pd-catalyzed C-C and C-N bond-forming cross-coupling reactions, its reactivity toward unreactive (hetero)aryl chlorides has been explored. We observed, in general, high yields in these transformations under mild conditions.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.