Metal-free Catalytic Olefin Hydrogenation: Low-Temperature H2 Activation by Frustrated Lewis Pairs†
Lutz Greb
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Department of Chemistry, University of Toronto, Ontario (Canada)
Search for more papers by this authorDr. Pascual Oña-Burgos
Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry, Karlsruhe (Germany)
Search for more papers by this authorBirgitta Schirmer
Organisch-Chemisches Institut, Universität Münster, Münster (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Stefan Grimme
Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
Stefan Grimme, Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
Jan Paradies, Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Search for more papers by this authorProf. Dr. Douglas W. Stephan
Department of Chemistry, University of Toronto, Ontario (Canada)
Search for more papers by this authorCorresponding Author
Dr. Jan Paradies
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Stefan Grimme, Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
Jan Paradies, Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Search for more papers by this authorLutz Greb
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Department of Chemistry, University of Toronto, Ontario (Canada)
Search for more papers by this authorDr. Pascual Oña-Burgos
Karlsruhe Institute of Technology (KIT), Institute of Inorganic Chemistry, Karlsruhe (Germany)
Search for more papers by this authorBirgitta Schirmer
Organisch-Chemisches Institut, Universität Münster, Münster (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Stefan Grimme
Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
Stefan Grimme, Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
Jan Paradies, Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Search for more papers by this authorProf. Dr. Douglas W. Stephan
Department of Chemistry, University of Toronto, Ontario (Canada)
Search for more papers by this authorCorresponding Author
Dr. Jan Paradies
Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Stefan Grimme, Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Universität Bonn, Beringstr. 4, 53115 Bonn (Germany)
Jan Paradies, Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber Weg 6, 76131 Karlsruhe (Germany)
Search for more papers by this authorThe 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.
Graphical Abstract
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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