Rhodium(II)‐Catalyzed Oxo‐Amination of Aryl Cyclopropanes

IF 2.7 3区 化学 Q2 CHEMISTRY, ORGANIC
Zhiying Fan , Nengde Liang , Yuanhua Wang
{"title":"Rhodium(II)‐Catalyzed Oxo‐Amination of Aryl Cyclopropanes","authors":"Zhiying Fan ,&nbsp;Nengde Liang ,&nbsp;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.
铑(II)催化芳基环丙烷氧胺化反应
我们描述了一种由芳基环丙烷合成β-氨基酮的铑(II)催化方法,利用水作为氧源,n -氟双苯磺酰胺(NFSI)作为商业可用的氮源。该方法在温和条件下具有良好的底物耐受性,为合成β-氨基酮提供了一条新颖实用的途径。机理研究揭示了一个顺序的级联途径,由铑(II)催化剂促进的单电子转移(SET)引发,然后是氢原子转移(HAT)和自由基极性交叉(RPC)步骤。这些见解强调了铑(II)在驱动自由基胺化反应方面的潜力,增强了从简单前体合成β-氨基酮的能力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
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.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术官方微信