Cu(II)-Azabis(oxazoline)-Complexes Immobilized on Superparamagnetic Magnetite@Silica-Nanoparticles: A Highly Selective and Recyclable Catalyst for the Kinetic Resolution of 1,2-Diols

Schaetz, Alexander and Hager, Markus and Reiser, Oliver (2009) Cu(II)-Azabis(oxazoline)-Complexes Immobilized on Superparamagnetic Magnetite@Silica-Nanoparticles: A Highly Selective and Recyclable Catalyst for the Kinetic Resolution of 1,2-Diols. ADVANCED FUNCTIONAL MATERIALS, 19 (13). pp. 2109-2115. ISSN 1616-301X, 1616-3028

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Abstract

Two different types of azide functionalized magnetite@silica nanoparticles are synthesized, which are ideally suited as inexpensive supports for catalysts and reagents as demonstrated with the grafting of copper(II)azabis(oxazoline) complexes via a copper(I) catalyzed azide/alkyne cycloaddition (CuAAC) reaction. The potential of the immobilized complexes as catalysts is tested in the desymmetrization of racemic 1,2-diols through asymmetric benzoylation. Compared to azabis(oxazolines) "clicked" to common polymeric supports such as MeOPEG or Merrifield resin, Fe3O4@SiO2 proves to be superior with respect to activity and selectivity, as exemplified by employing the catalysts in up to five runs with consistent high activity and selectivity. Recycling of the catalysts is achieved quantitatively by magnetic decantation.

Item Type: Article
Uncontrolled Keywords: CROSS-COUPLING REACTIONS; ASYMMETRIC CATALYSIS; POLYSTYRENE RESIN; ORGANIC CATALYSTS; TERMINAL ALKYNES; CLICK CHEMISTRY; AZIDE-ALKYNE; SOLID-PHASE; COMPLEXES; LIGANDS;
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Depositing User: Dr. Gernot Deinzer
Date Deposited: 10 Sep 2020 09:54
Last Modified: 10 Sep 2020 09:54
URI: https://pred.uni-regensburg.de/id/eprint/28704

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