Superhydrophobic, chiral, and mesoporous TsDPEN copolymer coordinated to ruthenium species as an efficient catalyst for asymmetric transfer hydrogenation
•Superhydrophobic, chiral, and mesoporous TsDPEN copolymer catalyst was synthesized.•The catalyst exhibits high activities and excellent recyclabilities in ATH reactions.•The catalyst shows better catalytic performance than the homogeneous catalyst.•The enhanced catalyst performance relates to reactant enrichment and product transfer.•The superhydrophobicity is responsible for reactant enrichment and product transfer.
SummaryHomogeneous chiral catalysts usually show higher catalytic activities than corresponding heterogeneous chiral catalysts, because of their easy interaction between catalytically active sites with reactant molecules. We demonstrate here superhydrophobic, chiral, and mesoporous catalysts (TsDPEN-Ru) synthesized from copolymerization of N-p-styrenesulfonyl-1,2-diphenylethylenediamine (V-TsDPEN) with divinylbenzene and loading of Ru species exhibiting much higher activities in asymmetric transfer hydrogenation (ATH) of ketones in aqueous solution than corresponding homogeneous chiral catalyst. This phenomenon is strongly related to the unique features of high enrichment for the reactants in superhydrophobic TsDPEN-Ru catalysts due to their good wettability, as well as easy transfer of product from the catalyst into water phase. These features open a door for design and developing a wide variety of chiral catalysts for asymmetric catalysis.
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Journal: - Volume 8, Issue 4, August 2013, Pages 342–350