Comparison of Superparamagnetic Fe3O4-Supported N-Heterocyclic Carbene-Based Catalysts for Enantioselective Allylation

Authors

  • Dr. Kalluri V. S. Ranganath,

    1. Organisch-Chemisches Institut, Westälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany), Fax: (+49) 25-83-33202
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  • Dr. Andreas H. Schäfer,

    1. nanoAnalytics GmbH, Heisenbergstraße 11, 48149 Münster (Germany)
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  • Prof. Dr. Frank Glorius

    Corresponding author
    1. Organisch-Chemisches Institut, Westälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany), Fax: (+49) 25-83-33202
    • Organisch-Chemisches Institut, Westälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany), Fax: (+49) 25-83-33202
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Abstract

original image

Once, twice, three times a catalyst: Iron oxide nanoparticles (NPs) were functionalized through a silane linker by a chiral imidazolium salt on the surface, a latent N-heterocyclic carbene precursor. This system was utilized in three ways in the enantioselective allylation of 4-nitrobenzaldehyde: as an organocatalyst (1); as a molecular metal complex catalyst (2), when together with [Pd(OAc)2]; and as a matrix for the formation of Pd NPs and, subsequently, as an active chiral NP catalyst (3). Enantiomeric excesses of up to 74 % were obtained.

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