title: Structure-Reactivity Relationship in the Frustrated Lewis Pair (FLP)-Catalyzed Hydrogenation of Imines.
abstract: The autoinduced, frustrated Lewis pair (FLP)-catalyzed hydrogenation of 16-benzene-ring substituted N-benzylidene-tert-butylamines with B(2,6-F2 C6 H3 )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.
authors.affiliation: Institute of Organic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Tussing
authors.affiliation: Institute of Organic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany.
authors.forename: Karl
authors.initials: K
authors.lastname: Kaupmees
authors.affiliation: Institute of Organic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany. jan.paradies@uni-paderborn.de.
authors.forename: Jan
authors.identifier: 0000-0002-3698-668X
authors.initials: J
authors.lastname: Paradies
keywords: Hammett correlation; autoinduced catalysis; frustrated Lewis pairs; hydrogenation; imines