<i>N</i>-Heterocyclic Carbene-Catalyzed [4 + 2] Annulation of Enolizable Thioesters for the Synthesis of 2-Pyrones

An <i>N</i>-heterocyclic carbene (NHC)-catalyzed [4 + 2] annulation enables the direct synthesis of 2-pyrones from α-chlorothioesters and β,γ-unsaturated α-keto esters or chalcones. The method utilizes NHC-activated α-chlorothioesters to generate key intermediates for 2-pyrone formation with high functional group tolerance. Moreover, the 2-pyrones were transformed into polysubstituted benzene and naphthalene derivatives, showcasing their synthetic value.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-23
DOI
https://doi.org/10.1021/acs.joc.5c00428
Citations
1
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
0.94

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article

N-Heterocyclic Carbene-Catalyzed [4 + 2] Annulation of Enolizable Thioesters for the Synthesis of 2-Pyrones

Jinfeng Zhang, Lixin Zhang, Hui Jin, Xu Cao et al.
1 citations
The Journal of Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
0.94
article

N-Heterocyclic Carbene-Catalyzed [4 + 2] Annulation of Enolizable Thioesters for the Synthesis of 2-Pyrones

Jinfeng Zhang, Lixin Zhang, Hui Jin, Xu Cao, Chen Zhu
article en
1 citations

Abstract

An <i>N</i>-heterocyclic carbene (NHC)-catalyzed [4 + 2] annulation enables the direct synthesis of 2-pyrones from α-chlorothioesters and β,γ-unsaturated α-keto esters or chalcones. The method utilizes NHC-activated α-chlorothioesters to generate key intermediates for 2-pyrone formation with high functional group tolerance. Moreover, the 2-pyrones were transformed into polysubstituted benzene and naphthalene derivatives, showcasing their synthetic value.

The Journal of Organic ChemistryVol. 90(17)
Shenyang University of Chemical Technology (CN)
Natural Science Foundation of Liaoning Province, Shenyang University of Chemical Technology
Openalex Percentile: Top 27%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
0.94
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