A Review on Generation and Reactivity of the N-Heterocyclic Carbene-Bound Alkynyl Acyl Azolium Intermediates

N-heterocyclic carbene (NHC) has been widely used as an organocatalyst for both umpolung and non-umpolung chemistry. Previous works mainly focus on species including Breslow intermediate, azolium enolate intermediate, homoenolate intermediate, alkenyl acyl azolium intermediate, etc. Notably, the NHC...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 22; p. 7990
Main Authors Dong, Ziyang, Jiang, Chengming, Zhao, Changgui
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 17.11.2022
MDPI
Subjects
Acids
alkynyl acyl azolium
annulation
Carbon
Catalysis
Chemical bonds
intermediate
mechanism
Methane - chemistry
N-heterocyclic carbene
Organic chemicals
Oxidation
Review
N-heterocyclic carbene
intermediate
alkynyl acyl azolium
annulation
mechanism
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Summary:N-heterocyclic carbene (NHC) has been widely used as an organocatalyst for both umpolung and non-umpolung chemistry. Previous works mainly focus on species including Breslow intermediate, azolium enolate intermediate, homoenolate intermediate, alkenyl acyl azolium intermediate, etc. Notably, the NHC-bound alkynyl acyl azolium has emerged as an effective intermediate to access functionalized cyclic molecular skeleton until very recently. In this review, we summarized the generation and reactivity of the NHC-bound alkynyl acyl azolium intermediates, which covers the efforts and advances in the synthesis of achiral and axially chiral cyclic scaffolds via the NHC-bound alkynyl acyl azolium intermediates. In particular, the mechanism related to this intermediate is discussed in detail.
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These authors contributed equally to this work.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27227990