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Updated: Sep 22, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
NHC-Catalyzed Transformation Reactions of Imines: Electrophilic versus Nucleophilic Attack
Chunhui Liu1, Peilin Han1, Xusheng Zhang1
1Key Laboratory of Micro-Nano Materials for Energy Storage and Conversion of Henan Province, Institute of Surface Micro and Nano Materials, College of Chemical and Materials Engineering, Xuchang University, Xuchang, Henan 461000, China.
Abstract:
It is generally accepted that N-heterocyclic carbene (NHC)-catalyzed imine transformations are initiated by a nucleophilic attack (NA) by NHC. However, due to significant nucleophilicity of the iminyl nitrogen atom in imines, the electrophilic attack (EA) by electrophiles onto imine would also be a possible mechanism of these kinds of reactions. Therefore, we use the quantum mechanical approach to disclose that both the NA and EA modes could be switchable for a wide range of NHC-catalyzed transformations of imines.
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