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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

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    Research Article

    CO2-Promoted Hydration of Propargylic Alcohols: Green Synthesis of α-Hydroxy Ketones by an Efficient and Recyclable AgOAc/Ionic Liquid System
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    • Di Li
      Di Li
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      School of Materials Science and Engineering, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      More by Di Li
    • Yanyan Gong
      Yanyan Gong
      State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250353, People’s Republic of China
      More by Yanyan Gong
    • Minchen Du
      Minchen Du
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      School of Materials Science and Engineering, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      More by Minchen Du
    • Chao Bu
      Chao Bu
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      School of Materials Science and Engineering, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      More by Chao Bu
    • Cheng Chen
      Cheng Chen
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      More by Cheng Chen
      Orcidhttp://orcid.org/0000-0001-5439-5421
    • Somboon Chaemcheun
      Somboon Chaemcheun
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      More by Somboon Chaemcheun
    • Jia Hu
      Jia Hu
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      School of Materials Science and Engineering, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      More by Jia Hu
    • Yongxing Zhang
      Yongxing Zhang
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      School of Materials Science and Engineering, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      More by Yongxing Zhang
    • Ye Yuan*
      Ye Yuan
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      *Email: [email protected]
      More by Ye Yuan
    • Francis Verpoort*
      Francis Verpoort
      State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      School of Materials Science and Engineering, Wuhan University of Technology, Wuhan 430070, People’s Republic of China
      National Research Tomsk Polytechnic University, Lenin Avenue 30, Tomsk 634050, Russian Federation
      Global Campus Songdo, Ghent University, 119 Songdomunhwa-Ro, Yeonsu-Gu, Incheon, Korea
      *Email: [email protected]
      More by Francis Verpoort
      Orcidhttp://orcid.org/0000-0002-5184-5500
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    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2020, 8, 22, 8148–8155
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    https://doi.org/10.1021/acssuschemeng.9b07546
    Published April 24, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    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.

    Copyright © 2020 American Chemical Society

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    • Optimization of the reaction conditions; investigation of the mechanism; investigation of the recyclability; characterization of the products (PDF)

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    This article is cited by 31 publications.

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    ACS Sustainable Chemistry & Engineering

    Cite this: ACS Sustainable Chem. Eng. 2020, 8, 22, 8148–8155
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acssuschemeng.9b07546
    Published April 24, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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