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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
Author(s) -
Schätz Alexander,
Hager Markus,
Reiser Oliver
Publication year - 2009
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.200801861
Subject(s) - kinetic resolution , oxazoline , catalysis , selectivity , desymmetrization , azide , materials science , copper , cycloaddition , alkyne , nanoparticle , reagent , magnetite , combinatorial chemistry , polymer chemistry , organic chemistry , chemistry , enantioselective synthesis , nanotechnology , metallurgy
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, Fe 3 O 4 @SiO 2 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.