CO2-Promoted Hydration of Propargylic Alcohols: Green Synthesis of α-Hydroxy Ketones by an Efficient and Recyclable AgOAc/Ionic Liquid System,ACS Sustainable Chemistry & Engineering

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CO2-Promoted Hydration of Propargylic Alcohols: Green Synthesis of α-Hydroxy Ketones by an Efficient and Recyclable AgOAc/Ionic Liquid System
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-04-24 , DOI: 10.1021/acssuschemeng.9b07546
Di Li _{1,

2} , Yanyan Gong ₃ , Minchen Du _{1,

2} , Chao Bu _{1,

2} , Cheng Chen ₁ , Somboon Chaemcheun ₁ , Jia Hu _{1,

2} , Yongxing Zhang _{1,

2} , Ye Yuan ₁ , Francis Verpoort _{1,

2,

4,

5}

Affiliation

α-Hydroxy ketones are a series of biologically active fragments in nature as well as important synthons for organic chemistry. Herein, an AgOAc/1-ethyl-3-methylimidazolium acetate ionic liquid system was developed for the CO₂-promoted hydration of propargylic alcohols and H₂O to produce α-hydroxy ketones. Diverse desired products could be obtained in satisfactory yields under 1 bar of CO₂ pressure with the catalysis of only a trace amount of silver (0.005–0.25 mol %), which is the lowest level ever reported for the metal-catalyzed systems. In particular, this system had robust recyclability, and it could be reused effectively at least 5 times. Furthermore, an unprecedented turnover number (TON) of 9200 was achieved, which is considered to be the highest TON ever reached for this hydration.

中文翻译：

CO ₂促进丙醇的水合：高效且可回收的AgOAc /离子液体系统绿色合成α-羟基酮

α-羟基酮是自然界中的一系列生物活性片段，也是有机化学的重要合成子。本文中，开发了AgOAc / 1-乙基-3-甲基咪唑鎓乙酸盐离子液体系统，用于CO ₂促进炔丙醇和H ₂ O的水合以产生α-羟基酮。在1 bar CO ₂下，可以以令人满意的产率获得各种所需产品催化只含痕量的银（0.005-0.25 mol％），这是金属催化体系中所报道的最低水平。特别是，该系统具有强大的可回收性，并且可以有效地重复使用至少5次。此外，获得了前所未有的9200营业额（TON），这被认为是该水合作用以来达到的最高TON。

更新日期：2020-04-24

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