Copper-Mediated Phosphoniumation of Aryl/Vinyl Boronic Acids

Following the successful construction of nitrilium/pyridinium and sulfonium salts, the Chan-Lam coupling has been significantly advanced with the first demonstration of quaternary phosphonium salt synthesis. We present a method employing copper(II) acetate in trifluoroethanol to efficiently produce a range of aryl and vinyl phosphonium salts from boronic acids, including those derived from complex natural products, thus overcoming phosphine oxidation issues and expanding the scope to functionalized phosphorus.

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Publication Details

Journal
Organic Letters
Published
2025-03-04
DOI
https://doi.org/10.1021/acs.orglett.5c00444
Citations
2
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Copper-Mediated Phosphoniumation of Aryl/Vinyl Boronic Acids

Xiaowen Zhan, Bin Liu, Zhongzheng Tian, Peng Liu et al.
2 citations
Organic Letters
Catalytic Cross-Coupling Reactions
1.87
article

Copper-Mediated Phosphoniumation of Aryl/Vinyl Boronic Acids

Xiaowen Zhan, Bin Liu, Zhongzheng Tian, Peng Liu, Zhibin Luo, Chao Hu, Dongchang Han, Ao Wen
article en
2 citations

Abstract

Following the successful construction of nitrilium/pyridinium and sulfonium salts, the Chan-Lam coupling has been significantly advanced with the first demonstration of quaternary phosphonium salt synthesis. We present a method employing copper(II) acetate in trifluoroethanol to efficiently produce a range of aryl and vinyl phosphonium salts from boronic acids, including those derived from complex natural products, thus overcoming phosphine oxidation issues and expanding the scope to functionalized phosphorus.

Organic LettersVol. 27(10)
Jiangsu University (CN)
National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 17%
Catalytic Cross-Coupling Reactions
1.87
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