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

Autor: Li, Xiaohong, Wang, Shenfan, Fu, Xiangxiang, Xing, Donghui, Fu, Zeyuan, Deng, Yuanfu, Jiang, Huanfeng, Huang, Liangbin
Zdroj: SCIENCE CHINA Chemistry; Sep2024, Vol. 67 Issue 9, p2975-2981, 7p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index