Synthesis of Stilbene Derivatives via Phosphine-Catalyzed Cascade [2+4] Annulation/Decarboxylative Aromatization of Yne-Enones with α-Pyrones

Despite significant advances in phosphine catalysis for synthesizing diverse cyclic frameworks, phosphine-catalyzed benzannulation reactions remain largely underexplored. In this work, we report a phosphine-catalyzed cascade [2+4] annulation/decarboxylative aromatization reaction between yne-enones and α-pyrones, which provides access to a wide range of functionalized stilbene derivatives in moderate to high yields (up to 98%). The reaction exhibits scalability and allows facile derivatization of products, highlighting its practical utility. A proposed mechanism outlines a stepwise annulation pathway and further underscores the unique reactivity of yne-enones in phosphine-catalyzed transformations.

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Publication Details

Journal
Organic Letters
Published
2026-02-13
DOI
https://doi.org/10.1021/acs.orglett.6c00564
Primary Topic
Catalytic Alkyne Reactions
Type
article
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article

Synthesis of Stilbene Derivatives via Phosphine-Catalyzed Cascade [2+4] Annulation/Decarboxylative Aromatization of Yne-Enones with α-Pyrones

Wing Yi Tang, Jingrong Jin, Bing Zheng, Zhiyang Cui et al.
Organic Letters
Catalytic Alkyne Reactions
article

Synthesis of Stilbene Derivatives via Phosphine-Catalyzed Cascade [2+4] Annulation/Decarboxylative Aromatization of Yne-Enones with α-Pyrones

Wing Yi Tang, Jingrong Jin, Bing Zheng, Zhiyang Cui, Hongchao Guo, Mingxia Huang, Leijie Zhou
article en

Abstract

Despite significant advances in phosphine catalysis for synthesizing diverse cyclic frameworks, phosphine-catalyzed benzannulation reactions remain largely underexplored. In this work, we report a phosphine-catalyzed cascade [2+4] annulation/decarboxylative aromatization reaction between yne-enones and α-pyrones, which provides access to a wide range of functionalized stilbene derivatives in moderate to high yields (up to 98%). The reaction exhibits scalability and allows facile derivatization of products, highlighting its practical utility. A proposed mechanism outlines a stepwise annulation pathway and further underscores the unique reactivity of yne-enones in phosphine-catalyzed transformations.

Organic LettersVol. 28(8)
China Agricultural University (CN)
Openalex Percentile: Top 55%
Catalytic Alkyne Reactions
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