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<i>N</i>‐Heterocyclic Carbenes (NHCs)‐Catalyzed Coupling Reactions of Aldehydes and Organic Halides

Fan Gao, Zengyu Zhang, Xiaoyu Yan

2023ChemCatChem16 citationsDOI

Abstract

Abstract This concept aims to summarize the direct coupling of aldehydes and organic halides (including activated and unactivated organic halides) catalyzed by N ‐heterocyclic carbenes (NHCs). The key factor of this transformation is the formation of Breslow intermediates, which are either nucleophilic or reductive. Additionally, the activation of inert C−H bond also was reviewed in this performance via the processes of single electron transfer (SET) and subsequent intramolecular 1, n ‐ hydrogen atom transfer (HAT) or intermolecular HAT. Finally, the key differences and reactivity of various Breslow intermediates, generated from different NHCs, have been discussed to give a deeper understanding of the ongoing popularity of NHC‐organocatalysis.

Topics & Concepts

ChemistryIntramolecular forceReactivity (psychology)CatalysisOrganocatalysisNucleophileOrganic synthesisHalideCarbeneElectron transferIntermolecular forceCombinatorial chemistryOrganic chemistryPhotochemistryMedicinal chemistryEnantioselective synthesisMoleculePathologyMedicineAlternative medicineN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods
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