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2022•The Journal of Organic ChemistryRequires access

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

Open publisher page 37 citations

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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What this paper is about

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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OpenAlex reports 37 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available 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.

Key concepts: Electrophile, Nucleophile, Chemistry, Imine, Catalysis, Carbene, Medicinal chemistry, Combinatorial chemistry

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