CO2-Promoted Hydration of Propargylic Alcohols: Green Synthesis of α-Hydroxy Ketones by an Efficient and Recyclable AgOAc/Ionic Liquid System

Di Li, Yanyan Gong, Minchen Du, Chao Bu, Cheng Chen, Somboon Chaemcheun, Jia Hu, Yongxing Zhang, Ye Yuan, Francis Verpoort

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)8148-8155
Number of pages8
JournalACS Sustainable Chemistry and Engineering
Volume8
Issue number22
DOIs
Publication statusPublished - 8 Jun 2020

Keywords

  • Carbon dioxide
  • Hydration
  • Ionic liquid
  • Silver catalysis
  • α-Hydroxy ketones

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

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