N-Heterocyclic Carbene-Catalyzed E1cB Elimination: A Strategy for Synthesizing Heteroaryl- <i>C</i> -Δ <sup>1,2</sup> -Glycosides

This work reports an unprecedented and efficient approach for the synthesis of a diverse range of heteroaryl-<i>C</i>-Δ<sup>1,2</sup>-glycosides via N-heterocyclic carbene (NHC)-catalyzed E1cB elimination. The method provides a highly practical, scalable, and broadly applicable strategy, delivering excellent yields across various substrates. Importantly, under the optimized conditions, numerous sensitive functional and protecting groups in the heteroaryl-<i>C</i>-Δ<sup>1,2</sup>-glycosides remained intact.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-03-02
DOI
https://doi.org/10.1021/acs.joc.5c03142
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
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article

N-Heterocyclic Carbene-Catalyzed E1cB Elimination: A Strategy for Synthesizing Heteroaryl- C -Δ 1,2 -Glycosides

Kai Luo, Li-Yan Hu, Feng Gang Li, Leling Song et al.
The Journal of Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

N-Heterocyclic Carbene-Catalyzed E1cB Elimination: A Strategy for Synthesizing Heteroaryl- C -Δ 1,2 -Glycosides

Kai Luo, Li-Yan Hu, Feng Gang Li, Leling Song, Fei Wang, Yan Lu, Lei Wu, Yan-Ping Guan, Zhi Li, Chong Li
article en

Abstract

This work reports an unprecedented and efficient approach for the synthesis of a diverse range of heteroaryl-<i>C</i>-Δ<sup>1,2</sup>-glycosides via N-heterocyclic carbene (NHC)-catalyzed E1cB elimination. The method provides a highly practical, scalable, and broadly applicable strategy, delivering excellent yields across various substrates. Importantly, under the optimized conditions, numerous sensitive functional and protecting groups in the heteroaryl-<i>C</i>-Δ<sup>1,2</sup>-glycosides remained intact.

The Journal of Organic ChemistryVol. 91(10)
Nanjing Agricultural University (CN), Zaozhuang University (CN)
Openalex Percentile: Top 37%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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