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Catalytic Hydrogenation Using Abnormal N-Heterocyclic Carbene Palladium Complexes: Catalytic Scope and Mechanistic Insights

Heckenroth, Marion; Khlebnikov, Vsevolod; Neels, Antonia; Schurtenberger, Peter LU and Albrecht, Martin (2011) In ChemCatChem 3(1). p.167-173
Abstract
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
abnormal bonding, carbene ligands, hydrogenation, mechanisms, palladium
in
ChemCatChem
volume
3
issue
1
pages
167 - 173
publisher
John Wiley & Sons
external identifiers
  • wos:000285888500021
  • scopus:80051803791
ISSN
1867-3880
DOI
10.1002/cctc.201000270
language
English
LU publication?
yes
id
5ff426fd-f3ef-44e3-bd63-7dc728bef105 (old id 1790818)
date added to LUP
2011-03-02 14:48:58
date last changed
2017-01-01 03:01:18
@article{5ff426fd-f3ef-44e3-bd63-7dc728bef105,
  abstract     = {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.},
  author       = {Heckenroth, Marion and Khlebnikov, Vsevolod and Neels, Antonia and Schurtenberger, Peter and Albrecht, Martin},
  issn         = {1867-3880},
  keyword      = {abnormal bonding,carbene ligands,hydrogenation,mechanisms,palladium},
  language     = {eng},
  number       = {1},
  pages        = {167--173},
  publisher    = {John Wiley & Sons},
  series       = {ChemCatChem},
  title        = {Catalytic Hydrogenation Using Abnormal N-Heterocyclic Carbene Palladium Complexes: Catalytic Scope and Mechanistic Insights},
  url          = {http://dx.doi.org/10.1002/cctc.201000270},
  volume       = {3},
  year         = {2011},
}