N‐Heterocyclic Carbene‐Catalyzed Umpolung Reactions of Imines Proceeding Through Aza‐Breslow Intermediates

N‐heterocyclic carbenes (NHCs) have emerged as efficient catalysts for promoting umpolung reactions of aldehydes and enals. Recently, the NHCs have been successfully used for catalyzing the umpolung reactions of aldimines through the formation of aza‐Breslow intermediates. This article provides a systematic review of the research progress in the polarity reversal of imines and related reactions catalyzed by NHCs, along with a detailed discussion and summary of the underlying reaction mechanisms. The review is organized and categorized according to the types of NHC‐catalyzed reactions involving imines.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-01-04
DOI
https://doi.org/10.1002/ejoc.202501171
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
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article

N‐Heterocyclic Carbene‐Catalyzed Umpolung Reactions of Imines Proceeding Through Aza‐Breslow Intermediates

Guihua Nie, Chengjiang Fang, Yu‐Guo Zheng, Jun Sun et al.
European Journal of Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

N‐Heterocyclic Carbene‐Catalyzed Umpolung Reactions of Imines Proceeding Through Aza‐Breslow Intermediates

Guihua Nie, Chengjiang Fang, Yu‐Guo Zheng, Jun Sun, Qianqian Guo, Mei Chen, Renfeng Zhang
article en

Abstract

N‐heterocyclic carbenes (NHCs) have emerged as efficient catalysts for promoting umpolung reactions of aldehydes and enals. Recently, the NHCs have been successfully used for catalyzing the umpolung reactions of aldimines through the formation of aza‐Breslow intermediates. This article provides a systematic review of the research progress in the polarity reversal of imines and related reactions catalyzed by NHCs, along with a detailed discussion and summary of the underlying reaction mechanisms. The review is organized and categorized according to the types of NHC‐catalyzed reactions involving imines.

European Journal of Organic ChemistryVol. 29(6)
Guizhou University (CN), Minzu Normal University of Xingyi (CN), Guizhou Academy of Testing & Analysis (CN)
Openalex Percentile: Top 97%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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