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 4.4 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2025-03-04 DOI:10.1002/adsc.202500103

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

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引用次数: 0

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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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.