Structure–Reactivity Relationship in the Frustrated Lewis Pair (FLP)‐Catalyzed Hydrogenation of Imines |
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| Authors: | Dipl‐Chem Sebastian Tussing Dr Karl Kaupmees Prof?Dr Jan Paradies |
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| Affiliation: | Institute of Organic Chemistry, University of Paderborn, Paderborn, Germany |
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| Abstract: | The autoinduced, frustrated Lewis pair (FLP)‐catalyzed hydrogenation of 16‐benzene‐ring substituted N‐benzylidene‐tert‐butylamines with B(2,6‐F2C6H3)3 and molecular hydrogen was investigated by kinetic analysis. The pKa values for imines and for the corresponding amines were determined by quantum‐mechanical methods and provided a direct proportional relationship. The correlation of the two rate constants k1 (simple catalytic cycle) and k2 (autoinduced catalytic cycle) with pKa difference between imine and amine pairs (ΔpKa) or Hammett's σ parameter served as useful parameters to establish a structure–reactivity relationship for the FLP‐catalyzed hydrogenation of imines. |
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| Keywords: | autoinduced catalysis frustrated Lewis pairs Hammett correlation hydrogenation imines |
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