Facile Synthesis of Hybrid Core–Shell Nanospheres for the Asymmetric Transfer Hydrogenation of Aromatic Ketones

Authors

  • Juan Wei,

    1. Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064 (P.R. China), Fax: (+86) 28-85412904
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  • Xiaomin Zhang,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China)
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  • Xiaoming Zhang,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China)
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  • Yaopeng Zhao,

    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China)
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  • Prof. Ruixiang Li,

    Corresponding author
    1. Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064 (P.R. China), Fax: (+86) 28-85412904
    • Ruixiang Li, Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064 (P.R. China), Fax: (+86) 28-85412904===

      Qihua Yang, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China)===

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  • Prof. Qihua Yang

    Corresponding author
    1. State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China)
    • Ruixiang Li, Key Lab of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan 610064 (P.R. China), Fax: (+86) 28-85412904===

      Qihua Yang, State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023 (P.R. China)===

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Abstract

The polymer–inorganic hybrid core–shell nanospheres with N-(para-toluenesulfonyl)-1,2-diphenylethylenediamine in the core and the poly(methyl acrylate) (PMA) polymer in the shell were prepared by using a sol–gel process. The surface properties of solid catalysts were modified by controlling PMA and the cetyltrimethylammonium bromide surfactant in the shell. The water contact angle results suggest that the presence of PMA and cetyltrimethylammonium bromide in the shell increases the surface hydrophobicity. In the Rh-catalyzed transfer hydrogenation of aromatic ketones in aqueous HCOONa, the solid catalyst with higher surface hydrophobicity demonstrates higher activity, which suggests that suitable surface properties increase the reaction rate by increasing the diffusion rates of hydrophobic substrates. Furthermore, this heterogeneous catalyst can be reused conveniently without loss of ee values.

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