Cu(OAc)<sub>2</sub>/TBPB-Mediated Cross-Dehydrogenative Coupling Reactions of Di/Trifluoromethylated <i>N</i>-Acylhydrazones with Diarylphosphine Oxides

A cross-dehydrogenative coupling reaction of fluoroalkylated <i>N</i>-acylhydrazones with diarylphosphine oxides is reported, which offers an effective route for the synthesis of phosphorylated di/trifluoromethylated N-acylhydrazones in moderate to excellent yields in the presence of Cu(OAc)<sub>2</sub>/TBPB. The method features a broad substrate scope. Mechanistic studies indicate that the reaction involves a radical CDC process between <i>N</i>-acylhydrazones and diarylphosphine oxides.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-08-04
DOI
https://doi.org/10.1021/acs.joc.5c00772
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Cu(OAc)2/TBPB-Mediated Cross-Dehydrogenative Coupling Reactions of Di/Trifluoromethylated N-Acylhydrazones with Diarylphosphine Oxides

Yulai Hu, Gaowang Yang, Ke‐Hu Wang, Danfeng Huang et al.
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Cu(OAc)2/TBPB-Mediated Cross-Dehydrogenative Coupling Reactions of Di/Trifluoromethylated N-Acylhydrazones with Diarylphosphine Oxides

Yulai Hu, Gaowang Yang, Ke‐Hu Wang, Danfeng Huang, Ying Fan, Peng Jin, Ruikang K. Wang, Zuyu Bai
article en

Abstract

A cross-dehydrogenative coupling reaction of fluoroalkylated <i>N</i>-acylhydrazones with diarylphosphine oxides is reported, which offers an effective route for the synthesis of phosphorylated di/trifluoromethylated N-acylhydrazones in moderate to excellent yields in the presence of Cu(OAc)<sub>2</sub>/TBPB. The method features a broad substrate scope. Mechanistic studies indicate that the reaction involves a radical CDC process between <i>N</i>-acylhydrazones and diarylphosphine oxides.

The Journal of Organic ChemistryVol. 90(32)
State Key Laboratory of Applied Organic Chemistry, Northwest Normal University (CN), Lanzhou University (CN)
National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 85%
Fluorine in Organic Chemistry
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Cu(OAc)<sub>2</sub>/TBPB-Mediated Cross-Dehydrogenative Coupling Reactions of Di/Trifluoromethylated <i>N</i>-Acylhydrazones with Diarylphosphine Oxides — Yulai Hu, Gaowang Yang, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS