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Heterogeneous Organocatalysis at Work: Functionalization of Hollow Periodic Mesoporous Organosilica Spheres with MacMillan Catalyst

Authors

  • Jiao Yi Shi,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 9318915557
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  • Chang An Wang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 9318915557
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  • Zhi Jun Li,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 9318915557
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  • Qiong Wang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 9318915557
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  • Yuan Zhang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 9318915557
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  • Prof. Dr. Wei Wang

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 9318915557
    • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 (P.R. China), Fax: (+86) 9318915557
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Abstract

We report a new method for the synthesis of hollow-structured phenylene-bridged periodic mesoporous organosilica (PMO) spheres with a uniform particle size of 100–200 nm using α-Fe2O3 as a hard template. Based on this method, the hollow-structured phenylene PMO could be easily functionalized with MacMillan catalyst (H-PhPMO-Mac) by a co-condensation process and a “click chemistry” post-modification. The synthesized H-PhPMO-Mac catalyst has been found to exhibit high catalytic activity (98 % yield, 81 % enantiomeric excess (ee) for endo and 81 % ee for exo) in asymmetric Diels–Alder reactions with water as solvent. The catalyst could be reused for at least seven runs without a significant loss of catalytic activity. Our results have also indicated that hollow-structured PMO spheres exhibit higher catalytic efficiency than solid (non-hollow) PMO spheres, and that catalysts prepared by the co-condensation process and “click chemistry” post-modification exhibit higher catalytic efficiency than those prepared by a grafting method.

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