Sustainable Synthesis of Acyl Fluoride via 1,3-Chelation-Assisted Transhalogenation and Its Application in the Valorization of Biomass-Derived Alcohol in Aqueous System

IF 3.7 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-05-27 Epub Date: 2025-03-21 DOI:10.1002/adsc.202500103

Geun Ho Kim, Do Hyeon Kim, Yeongjin Lee, Jung Woon Yang

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Abstract

We developed an environmentally friendly method for synthesizing acyl fluorides and achieving the selective mono-acylation of water-soluble alcohols using acyl fluorides in green media. Our method offers substantial advantages over the existing technologies for acyl fluoride production, particularly in terms of cost and environmental impact. Notably, our approach is augmented by an unusual 1,3-chelation via transhalogenation, and the use of an eco-friendly solvent and a simple base aligns with the principles of sustainable chemistry. We also explored the direct and highly efficient mono-acylation of biomass-derived water-soluble alcohols, such as ethylene glycol and glycerol, in the presence of water. The key arrangements, such as the role of the K₂CO₃ base and unusual 1,3-chelation between acyl fluoride and potassium ion, were characterized by HRMS and NMR spectroscopic analysis, and controlled experiments. These findings underscore the effectiveness of this method and provide deeper insights into the reaction mechanism.

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1,3螯合辅助转绿原化持续合成酰基氟及其在生物质衍生醇在水体系中的应用

我们开发了一种环境友好的方法来合成酰基氟化物，并在绿色介质中使用酰基氟化物实现了水溶性醇的选择性单酰化。与现有的酰基氟生产技术相比，我们的方法具有很大的优势，特别是在成本和环境影响方面。值得注意的是，我们的方法通过一种不寻常的1,3-螯合作用通过转绿原化得到了增强，并且使用了环保溶剂和简单的碱，符合可持续化学的原则。我们还探索了在存在水的情况下，生物质衍生的水溶性醇（如乙二醇和甘油）的直接和高效的单酰化。关键的安排，如K<；sub>2& gt; /sub>CO3；通过HRMS、NMR和对照实验表征了酰基氟与钾离子之间的不寻常的1,3螯合作用。这些发现强调了该方法的有效性，并对反应机制提供了更深入的了解。

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.