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Catalytic Hydrogenation Using Abnormal N‐Heterocyclic Carbene Palladium Complexes: Catalytic Scope and Mechanistic Insights
Author(s) -
Heckenroth Marion,
Khlebnikov Vsevolod,
Neels Antonia,
Schurtenberger Peter,
Albrecht Martin
Publication year - 2011
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201000270
Subject(s) - carbene , catalysis , palladium , alkene , chemistry , photochemistry , combinatorial chemistry , ligand (biochemistry) , transition metal carbene complex , organic chemistry , receptor , biochemistry
Palladium complexes containing abnormally bound C4‐bound dicarbene ligands have been exploited for catalytic alkene hydrogenation. Comparison to normally C2‐bound homologues indicates that the carbene bonding mode critically influences the catalytic activity. Good catalytic performance in the hydrogenation of cis ‐disubstituted olefins and non‐isomerizable terminal olefins under mild conditions (RT, 0.1 MPa H 2 ) only occurs when the carbene is abnormally bound to the palladium center. Detailed mechanistic investigations using dynamic light scattering in connection with time‐dependent analysis of conversions, and also performance of substoichiometric catalytic experiments provide evidence that the catalysis is heterogeneous and that the abnormally bound carbene ligand has the role of an activator.