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Selective Catalytic Oxidation of C[BOND]H Bonds with Molecular Oxygen

Authors

  • Prof. Emil Roduner,

    Corresponding author
    1. Institut für Physikalische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64495
    • Emil Roduner, Institut für Physikalische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64495

      Sabine Laschat, Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64285

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  • Prof. Wolfgang Kaim,

    1. Institut für Anorganische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany)
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  • Prof. Biprajit Sarkar,

    1. Institut für Anorganische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany)
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  • Prof. Vlada B. Urlacher,

    1. Institut für Biochemie der Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1,D-40225 Düsseldorf (Germany)
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  • Prof. Jürgen Pleiss,

    1. Institut für Technische Biochemie der Universität Stuttgart, Allmandring 31,D-70569 Stuttgart (Germany)
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  • Prof. Roger Gläser,

    1. Institut für Technische Chemie der Universität Leipzig, Linnéstr. 3,D-04103 Leipzig (Germany)
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  • Prof. Wolf-Dietrich Einicke,

    1. Institut für Technische Chemie der Universität Leipzig, Linnéstr. 3,D-04103 Leipzig (Germany)
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  • Prof. Georg A. Sprenger,

    1. Institut für Mikrobiologie der Universität Stuttgart, Allmandring 31,D-70569 Stuttgart (Germany)
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  • Prof. Uwe Beifuß,

    1. Institut für Chemie der Universität Hohenheim, Garbenstr. 30,D-70599 Stuttgart (Germany)
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  • Prof. Elias Klemm,

    1. Institut für Technische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany)
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  • Dr. Christian Liebner,

    1. Bundesanstalt für Materialforschung und -prüfung Unter den Eichen 87,D-12205 Berlin (Germany)
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  • Dr. Hartmut Hieronymus,

    1. Bundesanstalt für Materialforschung und -prüfung Unter den Eichen 87,D-12205 Berlin (Germany)
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  • Shih-Fan Hsu,

    1. Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64285
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  • Prof. Bernd Plietker,

    1. Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64285
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  • Prof. Sabine Laschat

    Corresponding author
    1. Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64285
    • Emil Roduner, Institut für Physikalische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64495

      Sabine Laschat, Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55,D-70569 Stuttgart (Germany), Fax: (+49) 711-685-64285

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Abstract

Although catalytic reductions, cross-couplings, metathesis, and oxidation of C[DOUBLE BOND]C double bonds are well established, the corresponding catalytic hydroxylations of C[BOND]H bonds in alkanes, arenes, or benzylic (allylic) positions, particularly with O2, the cheapest, “greenest”, and most abundant oxidant, are severely lacking. Certainly, some promising examples in homogenous and heterogenous catalysis exist, as well as enzymes that can perform catalytic aerobic oxidations on various substrates, but these have never achieved an industrial-scale, owing to a low space-time-yield and poor stability. This review illustrates recent advances in aerobic oxidation catalysis by discussing selected examples, and aims to stimulate further exciting work in this area. Theoretical work on catalyst precursors, resting states, and elementary steps, as well as model reactions complemented by spectroscopic studies provide detailed insight into the molecular mechanisms of oxidation catalyses and pave the way for preparative applications. However, O2 also poses a safety hazard, especially when used for large scale reactions, therefore sophisticated methodologies have been developed to minimize these risks and to allow convenient transfer onto industrial scale.

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