NHC-Catalyzed Transformation Reactions of Imines: Electrophilic versus Nucleophilic Attack
Chunhui Liu, Peilin Han, Xusheng Zhang, Yan Qiao, Zhi-Hong Xu, Yange Zhang, Dapeng Li, Donghui Wei, Yu Lan
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.
Topics & Concepts
ElectrophileNucleophileChemistryImineCatalysisCarbeneMedicinal chemistryCombinatorial chemistryOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods