The Azobis(isobutyronitrile)-Promoted Oxidative Radical α-Cyanation of Imine under Atmospheric O2

Autor: Zheng, Kui, Chen, Hailong, Zhao, Yang, Wang, Zhenlian, Cheng, Jiang
Zdroj: Organic Letters; October 2024, Vol. 26 Issue: 42 p9142-9145, 4p
Abstrakt: Herein, we report an azobis(isobutyronitrile) (AIBN)-promoted radical α-cyanation of in situformed imine under atmospheric O2. This oxidative radical addition (ORA) procedure proceeds with the sequential homocleavage of AIBN, extrusion of N2, and capture of O2toward an O-centered radical, which is converted to a cyano radical by β-scission. Then, the insertion of the cyano radical into the imine C═N bond forms an aminyl radical, leading to α-cyano imine after 1,2-hydrogen atom transfer (HAT) and H abstraction. Such a transition-metal-free procedure features mild reaction conditions and a broad substrate scope, employing molecular O2as a clean terminal oxidant.
Databáze: Supplemental Index