Palladium-Catalyzed Denitrative Mizoroki–Heck Reaction of Nitroarenes and Buta-1,3-dienes

A palladium-catalyzed denitrative Mizoroki-Heck reaction between nitroarenes and buta-1,3-dienes has been developed, enabling efficient synthesis of 1,4-diaryl-1,3-butadienes with a high functional group tolerance and moderate to excellent yields. Optimized conditions employing Pd(acac)<sub>2</sub>/BrettPhos as the catalyst in the presence of CsF in PhCF<sub>3</sub> facilitate selective terminal C-C coupling. The substrate scope encompasses diverse nitroarenes (electron-rich, -poor, heterocyclic) and dienes, demonstrating broad applicability. Postfunctionalization of products further underscores the method's utility in constructing complex aryl-substituted dienes.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-07-21
DOI
https://doi.org/10.1021/acs.joc.5c00972
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Palladium-Catalyzed Denitrative Mizoroki–Heck Reaction of Nitroarenes and Buta-1,3-dienes

Xuejie Wang, Wanzhi Chen
The Journal of Organic Chemistry
Catalytic Cross-Coupling Reactions
article

Palladium-Catalyzed Denitrative Mizoroki–Heck Reaction of Nitroarenes and Buta-1,3-dienes

Xuejie Wang, Wanzhi Chen
article en

Abstract

A palladium-catalyzed denitrative Mizoroki-Heck reaction between nitroarenes and buta-1,3-dienes has been developed, enabling efficient synthesis of 1,4-diaryl-1,3-butadienes with a high functional group tolerance and moderate to excellent yields. Optimized conditions employing Pd(acac)<sub>2</sub>/BrettPhos as the catalyst in the presence of CsF in PhCF<sub>3</sub> facilitate selective terminal C-C coupling. The substrate scope encompasses diverse nitroarenes (electron-rich, -poor, heterocyclic) and dienes, demonstrating broad applicability. Postfunctionalization of products further underscores the method's utility in constructing complex aryl-substituted dienes.

The Journal of Organic ChemistryVol. 90(30)
Zhejiang University (CN)
Openalex Percentile: Top 87%
Catalytic Cross-Coupling Reactions
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