SnCl<sub>2</sub>‐Catalyzed Phosphorylation of Alcohols and Selective Phosphorylation/Phosphinoylation of Carbohydrates

Phosphorylated molecules, particularly phosphorylated carbohydrates, have garnered significant interest due to their distinct biological activities, driving an urgent demand for efficient phosphorylation strategies. Herein, the successful development of a SnCl 2 ‐catalyzed protocol for the phosphorylation of alcohols and carbohydrates is demonstrated. Notably, the reaction efficiency is found to be critically dependent on the addition order of SnCl 2 and N , N ‐diisopropylethylamine, a phenomenon systematically investigated through mechanistic studies. A one‐pot sequential ketalization/phosphorylation strategy is established for polyol substrates, enabling streamlined access to phosphorylated derivatives. The versatility of this approach is further exemplified by achieving selective phosphorylation/phosphinoylation of carbohydrates.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-04-16
DOI
https://doi.org/10.1002/ejoc.202500209
Citations
2
Primary Topic
Organophosphorus compounds synthesis
Type
article
Field-Weighted Citation Impact
1.87

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article

SnCl2‐Catalyzed Phosphorylation of Alcohols and Selective Phosphorylation/Phosphinoylation of Carbohydrates

Hai Dong, Xiaorui Zhang, Jian Lv
2 citations
European Journal of Organic Chemistry
Organophosphorus compounds synthesis
1.87
article

SnCl2‐Catalyzed Phosphorylation of Alcohols and Selective Phosphorylation/Phosphinoylation of Carbohydrates

Hai Dong, Xiaorui Zhang, Jian Lv
article en
2 citations

Abstract

Phosphorylated molecules, particularly phosphorylated carbohydrates, have garnered significant interest due to their distinct biological activities, driving an urgent demand for efficient phosphorylation strategies. Herein, the successful development of a SnCl 2 ‐catalyzed protocol for the phosphorylation of alcohols and carbohydrates is demonstrated. Notably, the reaction efficiency is found to be critically dependent on the addition order of SnCl 2 and N , N ‐diisopropylethylamine, a phenomenon systematically investigated through mechanistic studies. A one‐pot sequential ketalization/phosphorylation strategy is established for polyol substrates, enabling streamlined access to phosphorylated derivatives. The versatility of this approach is further exemplified by achieving selective phosphorylation/phosphinoylation of carbohydrates.

European Journal of Organic ChemistryVol. 28(29)
Huazhong University of Science and Technology (CN), Wuhan Institute of Technology (CN)
Wuhan Institute of Technology
Openalex Percentile: Top 16%
Organophosphorus compounds synthesis
1.87
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