Work

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

Year: 2025

Type: article

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 SnCl2‐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 SnCl2 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.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500209

Authors: Jian Lv, Chun‐Yang Liu, Xiaorui Zhang, Shuang‐Xi Gu, Hai Dong

Institutions: Huazhong University of Science and Technology, Wuhan Institute of Technology

Language: English

Topic: Organophosphorus compounds synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funder: Wuhan Institute of Technology

Award: G8262684629