{"title":"Nickel-catalyzed arylcyanation of alkenes via cyano group translocation: access to 1,n-dinitriles or 4-amino nitriles","authors":"Xiaohong Li, Shenfan Wang, Xiangxiang Fu, Donghui Xing, Zeyuan Fu, Yuanfu Deng, Huanfeng Jiang, Liangbin Huang","doi":"10.1007/s11426-024-2006-1","DOIUrl":null,"url":null,"abstract":"<div><p>Herein, a nickel-catalyzed arylcyanation of unactivated alkenes <i>via</i> cyano group translocation with aryl boronic acids has been developed. These transformations provided a robust approach to constructing structurally diverse 1,<i>n</i>-dinitriles or 4-amino nitriles from easily prepared and commercially available starting materials. The cyano group translocation was achieved, involving the addition into the intramolecular C–N triple bond followed by the retro-Thorpe reaction. Mechanistic studies revealed that high temperature and CsHCO<sub>3</sub> as the base were crucial for the cyano group translocation.\n</p><div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":772,"journal":{"name":"Science China Chemistry","volume":"67 9","pages":"2975 - 2981"},"PeriodicalIF":10.4000,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Science China Chemistry","FirstCategoryId":"1","ListUrlMain":"https://link.springer.com/article/10.1007/s11426-024-2006-1","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, a nickel-catalyzed arylcyanation of unactivated alkenes via cyano group translocation with aryl boronic acids has been developed. These transformations provided a robust approach to constructing structurally diverse 1,n-dinitriles or 4-amino nitriles from easily prepared and commercially available starting materials. The cyano group translocation was achieved, involving the addition into the intramolecular C–N triple bond followed by the retro-Thorpe reaction. Mechanistic studies revealed that high temperature and CsHCO3 as the base were crucial for the cyano group translocation.
期刊介绍：
Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field.
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