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Nickel-catalyzed arylcyanation of alkenes via cyano group translocation: access to 1,n-dinitriles or 4-amino nitriles
Science China Chemistry ( IF 10.4 ) Pub Date : 2024-07-08 , DOI: 10.1007/s11426-024-2006-1
Xiaohong Li , Shenfan Wang , Xiangxiang Fu , Donghui Xing , Zeyuan Fu , Yuanfu Deng , Huanfeng Jiang , Liangbin Huang

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.



中文翻译:


通过氰基易位进行镍催化的烯烃芳氰化:获得 1,n-二腈或 4-氨基腈



在此,开发了一种镍催化的未活化烯烃通过氰基易位与芳基硼酸的芳基氰化反应。这些转化提供了一种从易于制备且市售的起始材料构建结构多样的 1,n-二腈或 4-氨基腈的可靠方法。实现了氰基易位,涉及加成到分子内 C-N 三键,然后进行逆索普反应。机理研究表明高温和CsHCO 3 作为碱基对于氰基易位至关重要。

更新日期:2024-07-11
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