Multifunctional Biomass-Based Ionic Liquids/CuCl-Catalyzed CO 2 -Promoted Hydration of Propargylic Alcohols: A Green Synthesis of α-Hydroxy Ketones.
Ye YuanSiqi ZhangKang DuanYong XuKaixuan GuoCheng ChenSomboon ChaemchuenDongfeng CaoFrancis VerpoortPublished in: International journal of molecular sciences (2024)
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 2 SO 4 as catalysts, resulting in harsh conditions and the undesired side reaction of Meyer-Schuster rearrangement. In this study, CO 2 -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 2 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 2 and the Cu component.