Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones
α-Hydroxy ketones are a class of vital organic skeletons that generally exist in a variety of natural products and high-value chemicals. However, the traditional synthetic route for their production involves toxic Hg salts and corrosive H<sub>2</sub>SO<sub>4</sub> as catalyst...
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2024-02-01
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| Series: | International Journal of Molecular Sciences |
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| author | Ye Yuan Siqi Zhang Kang Duan Yong Xu Kaixuan Guo Cheng Chen Somboon Chaemchuen Dongfeng Cao Francis Verpoort |
| author_facet | Ye Yuan Siqi Zhang Kang Duan Yong Xu Kaixuan Guo Cheng Chen Somboon Chaemchuen Dongfeng Cao Francis Verpoort |
| author_sort | Ye Yuan |
| collection | DOAJ |
| description | α-Hydroxy ketones are a class of vital organic skeletons that generally exist in a variety of natural products and high-value chemicals. However, the traditional synthetic route for their production involves toxic Hg salts and corrosive H<sub>2</sub>SO<sub>4</sub> as catalysts, resulting in harsh conditions and the undesired side reaction of Meyer–Schuster rearrangement. In this study, CO<sub>2</sub>-promoted hydration of propargylic alcohols was achieved for the synthesis of various α-hydroxy ketones. Notably, this process was catalyzed using an environmentally friendly and cost-effective biomass-based ionic liquids/CuCl system, which effectively eliminated the side reaction. The ionic liquids utilized in this system are derived from natural biomass materials, which exhibited recyclability and catalytic activity under 1 bar of CO<sub>2</sub> pressure without volatile organic solvents or additives. Evaluation of the green metrics revealed the superiority of this CuCl/ionic liquid system in terms of environmental sustainability. Further mechanistic investigation attributed the excellent performance to the ionic liquid component, which exhibited multifunctionality in activating substrates, CO<sub>2</sub> and the Cu component. |
| first_indexed | 2024-03-08T03:54:25Z |
| format | Article |
| id | doaj.art-30f138b878714998a00880460d19c123 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-08T03:54:25Z |
| publishDate | 2024-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-30f138b878714998a00880460d19c1232024-02-09T15:15:18ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672024-02-01253193710.3390/ijms25031937Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy KetonesYe Yuan0Siqi Zhang1Kang Duan2Yong Xu3Kaixuan Guo4Cheng Chen5Somboon Chaemchuen6Dongfeng Cao7Francis Verpoort8State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, ChinaSchool of Material Science and Engineering, Wuhan University of Technology, Wuhan 430070, ChinaSchool of Material Science and Engineering, Wuhan University of Technology, Wuhan 430070, ChinaSchool of Material Science and Engineering, Wuhan University of Technology, Wuhan 430070, ChinaSchool of Material Science and Engineering, Wuhan University of Technology, Wuhan 430070, ChinaState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, ChinaState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, ChinaState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, ChinaState Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, Chinaα-Hydroxy ketones are a class of vital organic skeletons that generally exist in a variety of natural products and high-value chemicals. However, the traditional synthetic route for their production involves toxic Hg salts and corrosive H<sub>2</sub>SO<sub>4</sub> as catalysts, resulting in harsh conditions and the undesired side reaction of Meyer–Schuster rearrangement. In this study, CO<sub>2</sub>-promoted hydration of propargylic alcohols was achieved for the synthesis of various α-hydroxy ketones. Notably, this process was catalyzed using an environmentally friendly and cost-effective biomass-based ionic liquids/CuCl system, which effectively eliminated the side reaction. The ionic liquids utilized in this system are derived from natural biomass materials, which exhibited recyclability and catalytic activity under 1 bar of CO<sub>2</sub> pressure without volatile organic solvents or additives. Evaluation of the green metrics revealed the superiority of this CuCl/ionic liquid system in terms of environmental sustainability. Further mechanistic investigation attributed the excellent performance to the ionic liquid component, which exhibited multifunctionality in activating substrates, CO<sub>2</sub> and the Cu component.https://www.mdpi.com/1422-0067/25/3/1937ionic liquidCO<sub>2</sub>biomasscatalysisα-hydroxy ketones |
| spellingShingle | Ye Yuan Siqi Zhang Kang Duan Yong Xu Kaixuan Guo Cheng Chen Somboon Chaemchuen Dongfeng Cao Francis Verpoort Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones International Journal of Molecular Sciences ionic liquid CO<sub>2</sub> biomass catalysis α-hydroxy ketones |
| title | Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones |
| title_full | Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones |
| title_fullStr | Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones |
| title_full_unstemmed | Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones |
| title_short | Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO<sub>2</sub>-Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones |
| title_sort | multifunctional biomass based ionic liquids cucl catalyzed co sub 2 sub promoted hydration of propargylic alcohols a green synthesis of α hydroxy ketones |
| topic | ionic liquid CO<sub>2</sub> biomass catalysis α-hydroxy ketones |
| url | https://www.mdpi.com/1422-0067/25/3/1937 |
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