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Updated: Nov 3, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Transition-metal-free C(sp3)-H/C(sp3)-H dehydrogenative coupling of saturated heterocycles with N-benzyl imines
Zhengfen Liu1, Minyan Li2, Guogang Deng1
1Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education and Yunnan Province, State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology, Yunnan University Kunming 650091 P. R. China xdyang@ynu.edu.cn zhanghb@ynu.edu.cn.
Abstract:
A unique C(sp3)-H/C(sp3)-H dehydrocoupling of N-benzylimines with saturated heterocycles is described. Using super electron donor (SED) 2-azaallyl anions and aryl iodides as electron acceptors, single-electron-transfer (SET) generates an aryl radical. Hydrogen atom transfer (HAT) from saturated heterocycles or toluenes to the aryl radical generates alkyl radicals or benzylic radicals, respectively. The newly formed alkyl radicals and benzylic radicals couple with the 2-azaallyl radicals with formation of new C-C bonds. Experimental evidence supports the key hydrogen-abstraction by the aryl radical, which determines the chemoselectivity of the radical-radical coupling reaction. It is noteworthy that this procedure avoids the use of traditional strong oxidants and transition metals.
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