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Functionalized Periodic Mesoporous Organosilica: A Highly Enantioselective Catalyst for the Michael Addition of 1,3-Dicarbonyl Compounds to Nitroalkenes

Authors

  • Ketang Liu,

    1. Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China)
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  • Ronghua Jin,

    1. Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China)
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  • Tanyu Cheng,

    1. Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China)
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  • Xiangming Xu,

    1. Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China)
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  • Fei Gao,

    1. Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China)
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  • Prof. Guohua Liu,

    Corresponding author
    1. Key Laboratory of Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China), Fax: (+86) 2164321819
    • Key Laboratory of Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China), Fax: (+86) 2164321819
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  • Prof. Hexing Li

    Corresponding author
    1. Key Laboratory of Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China), Fax: (+86) 2164321819
    • Key Laboratory of Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, No.100 Guilin Rd., Shanghai 200234 (P.R. China), Fax: (+86) 2164321819
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Abstract

A functionalized periodic mesoporous organosilica with incorporated chiral bis(cyclohexyldiamine)-based NiII complexes within the silica framework was developed by the co-condensation of (1R,2R)-cyclohexyldiamine-derived silane and ethylene-bridge silane, followed by the complexation of NiBr2 in the presence of (1R,2R)-N,N′-dibenzylcyclohexyldiamine. Structural characterization by XRD, nitrogen sorption, and TEM disclosed its orderly mesostructure, and FTIR and solid-state NMR spectroscopy demonstrated the incorporation of well-defined single-site bis(cyclohexyldiamine)-based NiII active centers within periodic mesoporous organosilica. As a chiral heterogeneous catalyst, this functionalized periodic mesoporous organosilica showed high catalytic activity and excellent enantioselectivity in the asymmetric Michael addition of 1,3-dicarbonyl compounds to nitroalkenes, comparable to those with homogeneous catalysts. In particular, this heterogeneous catalyst could be recovered easily and reused repeatedly up to nine times without obviously affecting its enantioselectivity, thus showing good potential for industrial applications.

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