Nickel-catalyzed arylcyanation of alkenes via cyano group translocation: access to 1,n-dinitriles or 4-amino nitriles

IF 10.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Science China Chemistry 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

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.

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镍催化的芳基氰化烯通过氰基易位：获得 1,n-二腈纶或 4-氨基腈纶

在此，研究人员开发了一种镍催化的芳基氰化反应，通过氰基与芳基硼酸的易位反应，将未活化的烯烃转化为芳基硼酸。这些转化提供了一种稳健的方法，利用易于制备且市场上可买到的起始材料构建结构多样的 1,n-二腈或 4-氨基腈。氰基转位的实现涉及到分子内 C-N 三键的加成，然后是逆托普反应。机理研究表明，高温和以 CsHCO3 为碱基是氰基转移的关键。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Science China Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

7.30%

发文量

3787

审稿时长

2.2 months

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. Categories of articles include: Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry. Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies. Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.