Shao-Jie Cheng, Xin-Li Zhang, Zhen-Xu Yang, Ai-Hua Wang, Zhi-Shi Ye
{"title":"Palladium-Catalyzed N-Allylic Alkylation of Pyrazoles and Unactivated Vinylcyclopropanes","authors":"Shao-Jie Cheng, Xin-Li Zhang, Zhen-Xu Yang, Ai-Hua Wang, Zhi-Shi Ye","doi":"10.1021/acs.orglett.4c03808","DOIUrl":null,"url":null,"abstract":"An efficient palladium-catalyzed <i>N</i>-allylic alkylation of pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording various <i>N</i>-alkyl pyrazoles in ≤99% yield. This protocol displays high atom economy, a broad range of substrates, and excellent regioselectivity and stereoselectivity. Late-stage modification of bioactive molecules, scaled-up reaction, and divergent derivatization documented the practicability of this methodology. The preliminary mechanistic investigation hinted that the Pd–H species promotes the ring opening of cyclopropanes.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"44 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2024-12-20","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.4c03808","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
An efficient palladium-catalyzed N-allylic alkylation of pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording various N-alkyl pyrazoles in ≤99% yield. This protocol displays high atom economy, a broad range of substrates, and excellent regioselectivity and stereoselectivity. Late-stage modification of bioactive molecules, scaled-up reaction, and divergent derivatization documented the practicability of this methodology. The preliminary mechanistic investigation hinted that the Pd–H species promotes the ring opening of cyclopropanes.
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.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
