Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 29, Pages 10009-10016Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600386
Keywords
density functional calculations; homogeneous catalysis; hydrogenation; Lewis acids; transfer hydrogenation
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Funding
- Swiss National Science Foundation
- Deutsche Forschungsgemeinschaft [SFB 813]
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Hydrogenation and transfer hydrogenation of imines with cyclohexa-1,4-dienes, as well as with a representative Hantzsch ester dihydrogen surrogate, are reported. Both processes are catalyzed by tethered Ru-S complexes but differ in the activation mode of the dihydrogen source: cooperative activation of the H-H bond at the Ru-S bond leads to the corresponding Ru-H complex and protonation of the sulfur atom, whereas the same cationic Ru-S catalyst abstracts a hydride from a donor-substituted cyclohexa-1,4-diene to form the neutral Ru-H complex and a low-energy Wheland intermediate. A sequence of proton and hydride transfers on the imine substrate then yields an amine. The reaction pathways are analyzed computationally, and the established mechanistic pictures are in agreement with the experimental observations.
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