Brønsted Base-Catalyzed Phosphorylation of Alkynes via Vinylidene <i>p</i>-Quinone Methides

Vinylphosphonates serve as crucial components in synthetic chemistry, medicinal chemistry, and materials science. However, traditional synthetic methods for these compounds typically require the use of noble metal catalysts and hazardous reagents. Herein, we report a metal-free strategy for the divergent synthesis of vinylphosphonates through the P nucleophilic addition of vinylidene <i>p</i>-quinone methides (<i>p</i>-VQMs). This method provides a variety of 1,2-diaryl vinylphosphates in good yields (up to 85% yield), which represents a unique example of <i>p</i>-VQMs for C-P bond formation. The protocol features mild reaction conditions, a green solvent, broad functional group compatibility, and environmental friendliness.

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Publication Details

Journal
Organic Letters
Published
2025-09-09
DOI
https://doi.org/10.1021/acs.orglett.5c03542
Citations
1
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
0.94
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article

Brønsted Base-Catalyzed Phosphorylation of Alkynes via Vinylidene p-Quinone Methides

Jun Jiang, Cui‐Wu Lin, Xiu Gu, Meng Gong et al.
1 citations
Organic Letters
Synthesis of Indole Derivatives
0.94
article

Brønsted Base-Catalyzed Phosphorylation of Alkynes via Vinylidene p-Quinone Methides

Jun Jiang, Cui‐Wu Lin, Xiu Gu, Meng Gong, Nan Huang
article en
1 citations

Abstract

Vinylphosphonates serve as crucial components in synthetic chemistry, medicinal chemistry, and materials science. However, traditional synthetic methods for these compounds typically require the use of noble metal catalysts and hazardous reagents. Herein, we report a metal-free strategy for the divergent synthesis of vinylphosphonates through the P nucleophilic addition of vinylidene <i>p</i>-quinone methides (<i>p</i>-VQMs). This method provides a variety of 1,2-diaryl vinylphosphates in good yields (up to 85% yield), which represents a unique example of <i>p</i>-VQMs for C-P bond formation. The protocol features mild reaction conditions, a green solvent, broad functional group compatibility, and environmental friendliness.

Organic LettersVol. 27(37)
Guangxi University (CN)
Openalex Percentile: Top 22%
Synthesis of Indole Derivatives
0.94
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