Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 22, Pages 8056-8059Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500805
Keywords
autoinduced catalysis; frustrated Lewis pairs; hydrogen activation; inverse equilibrium isotope effect; kinetics
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Funding
- Landesgraduiertenforderung of the State of Baden-Wurttemberg
- German Science Foundation (DFG)
- DFG
- HGF programme BIFTM
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The frustrated Lewis pair (FLP)-catalyzed hydrogenation and deuteration of N-benzylidene-tert-butylamine (2) was kinetically investigated by using the three boranes B(C6F5)(3) (1), B(2,4,6-F-3-C6H2)(3) (4), and B(2,6-F-2-C6H3)(3) (5) and the free activation energies for the H-2 activation by FLP were determined. Reactions catalyzed by the weaker Lewis acids 4 and 5 displayed autoinductive catalysis arising from a higher free activation energy (2kcalmol(-1)) for the H-2 activation by the imine compared to the amine. Surprisingly, the imine reduction using D-2 proceeded with higher rates. This phenomenon is unprecedented for FLP and resulted from a primary inverse equilibrium isotope effect.
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