Metal-free Catalytic Olefin Hydrogenation: Low-Temperature H2 Activation by Frustrated Lewis Pairs

Authors

  • Lutz Greb,

    1. Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
    2. Department of Chemistry, University of Toronto, Ontario (Canada)
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  • Dr. Pascual Oña-Burgos,

    1. Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry, Karlsruhe (Germany)
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  • Birgitta Schirmer,

    1. Organisch-Chemisches Institut, Universität Münster, Münster (Germany)
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  • Prof. Dr. Stefan Grimme,

    Corresponding author
    1. Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
    • Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
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  • Prof. Dr. Douglas W. Stephan,

    1. Department of Chemistry, University of Toronto, Ontario (Canada)
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  • Dr. Jan Paradies

    Corresponding author
    1. Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
    • Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
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  • The LGF, FCI, and AvH are gratefully acknowledged by L.G., J.P., and P.O.B. for financial support. J.P. thanks S. Bräse and F. Breher for kind support and fruitful discussions. B.S., S.G., and D.W.S. gratefully acknowledge the financial support from the DFG-SNF 1175 and NSERC of Canada for the award of a Canada Research Chair.

Abstract

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Weak nucleophiles for strong activation: The reversible activation of dihydrogen by an electron-deficient phosphine, (C6F5)PPh2, in combination with the Lewis acid B(C6F5)3 at −80 °C was accomplished. The catalytic hydrogenation of olefins proceeds through protonation and subsequent hydride attack. Electron-deficient phosphines and diarlyamines were demonstrated to be viable Lewis bases for the reaction, thus allowing catalyst loadings of 10 to 5 mol %.

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