Related Experiment Video
Updated: Jun 10, 2025

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
Experimental Evidence for Zerovalent Pd(NHC) as a Competent Catalyst in C-N Cross-Coupling (NHC = DiMeIHeptCl)
Volodymyr Semeniuchenko1,2, Sepideh Sharif3, Neha Rana3
1Centre for Catalysis Research and Innovation (CCRI), Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Ontario K1N 6N5, Canada.
Abstract:
Use of the branched N-heterocyclic carbene (NHC) ligand 1,3-bis(2,6-bis(3-methyl-1-(2-methylpropyl)butyl)phenyl)-4,5-dichloro-1,3-dihydro-2H-imidazole-2-ylidene (DiMeIHeptCl) facilitated the stabilization of several relevant intermediates for Pd(NHC)-catalyzed C-N cross-coupling reactions. Complexes [Pd(DiMeIHeptCl)]2(μ-N2), [Pd(DiMeIHeptCl)]2(μ-η2-1,2-η2-4,5-C6H6), and Pd(DiMeIHeptCl)(pyridine), representing zerovalent Pd(NHC) bearing labile ligands, were isolated and structurally characterized, along with divalent PdCl(Ph)(DiMeIHeptCl) and PdCl(Ph)(DiMeIHeptCl)(n-propylamine). The former is a 14-electron Pd complex, which is stable under air and chromatography on silica gel or neutral alumina. One possible reason for this exceptional stability is the numerous dispersion interactions between the NHC alkyl chains and the Pd-Ph group. Detailed investigations of catalyst activation and oxidative addition confirmed that "Pd(NHC)" is formed from many known Pd(II)(NHC) precatalysts and provided activation rates for these different precatalysts.
More Related Videos
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
10:19Synthesis and Testing of Supported Pt-Cu Solid Solution Nanoparticle Catalysts for Propane Dehydrogenation
Published on: July 18, 2017
Related Concept Videos
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Nucleophilic Aromatic Substitution: Elimination–Addition
Reduction of Alkenes: Catalytic Hydrogenation
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Catalysis
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H