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Updated: Jun 10, 2025

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The Azobis(isobutyronitrile)-Promoted Oxidative Radical α-Cyanation of Imine under Atmospheric O2
Kui Zheng1, Hailong Chen1, Yang Zhao1
1College of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. China.
Abstract:
Herein, we report an azobis(isobutyronitrile) (AIBN)-promoted radical α-cyanation of in situ formed imine under atmospheric O2. This oxidative radical addition (ORA) procedure proceeds with the sequential homocleavage of AIBN, extrusion of N2, and capture of O2 toward 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 O2 as a clean terminal oxidant.
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