{"title":"Rhodium(II)‐Catalyzed Oxo‐Amination of Aryl Cyclopropanes","authors":"Zhiying Fan , Nengde Liang , Yuanhua Wang","doi":"10.1002/ejoc.202500235","DOIUrl":null,"url":null,"abstract":"<div><div>A rhodium(II)‐catalyzed method is described for synthesizing β‐amino ketones from aryl cyclopropanes, utilizing water as an oxygen source and <em>N</em>‐fluorobis(benzenesulfonamide) as a commercially available nitrogen source. This approach offers good substrate tolerance under mild conditions, providing a novel and practical route for β‐amino ketone synthesis. Mechanistic studies reveal a sequential cascade pathway initiated by single‐electron transfer facilitated by the rhodium(II) catalyst, followed by hydrogen atom transfer and radical polar crossover steps. These insights underscore the potential of rhodium(II) in driving radical amination reactions, enhancing the synthesis of β‐amino ketones from simple precursors.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 23","pages":"Article e202500235"},"PeriodicalIF":2.7000,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X2500249X","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A rhodium(II)‐catalyzed method is described for synthesizing β‐amino ketones from aryl cyclopropanes, utilizing water as an oxygen source and N‐fluorobis(benzenesulfonamide) as a commercially available nitrogen source. This approach offers good substrate tolerance under mild conditions, providing a novel and practical route for β‐amino ketone synthesis. Mechanistic studies reveal a sequential cascade pathway initiated by single‐electron transfer facilitated by the rhodium(II) catalyst, followed by hydrogen atom transfer and radical polar crossover steps. These insights underscore the potential of rhodium(II) in driving radical amination reactions, enhancing the synthesis of β‐amino ketones from simple precursors.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.