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Mimicking Ozonolysis via Mechanochemistry: Internal Alkynes to 1,2-Diketones using H5IO6
Chemistry - A European Journal ( IF 4.3 ) Pub Date : 2024-04-18 , DOI: 10.1002/chem.202401027
Pravat Nayek 1 , Prasenjit Mal 2
Affiliation  

Utilizing periodic acid as an environmentally benign oxidizing agent, this study introduces a novel mechanochemical method that mimics ozonolysis to convert internal alkynes into 1,2-diketones, showcasing effective emulation of ozone's reactivity. Notably, this oxidation occurs at room temperature in aerobic conditions, eliminating the need for toxic transition metals, hazardous oxidants, or expensive solvents. Through control experiments validating the mechanism, substantial evidence supports a concerted reaction pathway. This progress marks a significant stride toward cleaner and more efficient chemical synthesis, mitigating the environmental impact of conventional processes. Assessing the green chemistry metrics in both solvent-free and previously reported solvent-based methods, our eco-friendly protocol demonstrates an E-factor of 7.40, a 51.7% atom economy, a 45.5% atom efficiency, 100% carbon efficiency, and 11.9% reaction mass efficiency when solvents are not used.

中文翻译:

通过机械化学模拟臭氧分解:使用 H5IO6 将内部炔烃转化为 1,2-二酮

本研究利用高碘酸作为一种环境友好的氧化剂,引入了一种模拟臭氧分解的新型机械化学方法,将内部炔烃转化为 1,2-二酮,展示了对臭氧反应性的有效模拟。值得注意的是,这种氧化在室温有氧条件下发生,无需使用有毒的过渡金属、危险的氧化剂或昂贵的溶剂。通过验证该机制的对照实验,大量证据支持一致的反应途径。这一进展标志着向更清洁、更高效的化学合成迈出了一大步,减轻了传统工艺对环境的影响。评估无溶剂和先前报道的基于溶剂的方法中的绿色化学指标,我们的环保协议显示 E 因子为 7.40、51.7% 原子经济性、45.5% 原子效率、100% 碳效率和 11.9不使用溶剂时的%反应质量效率。
更新日期:2024-04-18
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