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Preparation of a N-Heterocyclic Carbene Nickel(II) Complex. Synthetic Experiments in Current Organic and Organometallic Chemistry
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Abstract
A four-part experiment that leads to the synthesis of a cyclopentadienyl chloro–nickel(II) complex bearing a N-heterocyclic carbene (NHC) ligand is presented. In the first part, the preparation of 1,3-bis-(2,4,6-trimethylphenyl)imidazolium chloride (IMes·HCl) in a one-pot procedure by reaction of 2,4,6-trimethylaniline with paraformaldehyde, glyoxal, and hydrochloric acid is described. The reaction of NiCl2·6H2O with aqueous ammonia to give [Ni(NH3)6]Cl2, and the reaction of sodium in neat dicyclopentadiene at 160 °C to produce sodium cyclopentadienide in a one-pot synthesis are both delineated in the second part of this experiment. The reaction of [Ni(NH3)6]Cl2, with NaCp to yield [Ni(η5-C5H5)2] forms the third part. Finally, the procedure ends with the reaction of nickelocene with IMes·HCl to afford the nickel(II) half-sandwich complex [Ni(η5-C5H5)(IMes)Cl]. This sequence of experiments provides an excellent example of NHC–ligand preparation and its subsequent complexation to a transition metal and is appropriate for an advanced undergraduate or a graduate lab course. It also provides an opportunity for students to learn standard Schlenk techniques. Furthermore, the characterization of some of the products by 1H NMR spectroscopy demonstrates the utility of 1H NMR in both organic and organometallic chemistry.
Keywords (Audience):
Graduate Education / ResearchKeywords (Domain):
Inorganic ChemistryKeywords (Pedagogy):
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
Synthesis and Catalytic Activity in Suzuki Coupling of Nickel Complexes Bearing n-Butyl- and Triethoxysilylpropyl-Substituted NHC Ligands: Toward the Heterogenization of Molecular Catalysts
Anna Magdalena Oertel, Vincent Ritleng, and Michael J. ChetcutiOrganometallics2012 31 (7), 2829-2840Synthesis and Catalytic Activity in Suzuki Coupling of Nickel Complexes Bearing n-Butyl- and Triethoxysilylpropyl-Substituted NHC Ligands: Toward the Heterogenization of Molecular Catalysts
Anna Magdalena Oertel, Vincent Ritleng, and Michael J. ChetcutiOrganometallics2012 31 (7), 2829-2840Cyclopentadienyl N-heterocyclic carbene (NHC) nickel complexes of general formula [Ni(R-NHC-nBu)XCp] [R-NHC-nBu = 1-butyl-3-methyl-, 1-isopropyl-3-butyl-, 1-phenyl-3-butyl-, 1-(2,4,6-trimethylphenyl)-3-butyl-, 1-(2,6-diisopropylphenyl)-3-butyl-imidazol-2-...
Intramolecular Nitrile C–H Bond Activation in Nickel NHC Complexes: A Route to New Nickelacycles
Anna Magdalena Oertel, Julien Freudenreich, Jordan Gein, Vincent Ritleng, Luis F. Veiros, and Michael J. ChetcutiOrganometallics2011 30 (12), 3400-3411Intramolecular Nitrile C–H Bond Activation in Nickel NHC Complexes: A Route to New Nickelacycles
Anna Magdalena Oertel, Julien Freudenreich, Jordan Gein, Vincent Ritleng, Luis F. Veiros, and Michael J. ChetcutiOrganometallics2011 30 (12), 3400-3411Cyclopentadienyl N-heterocyclic carbene (NHC) nickel complexes of general formula [Ni(NHC)XCp] (NHC = 1-(propylnitrile)-3-methylimidazol-2-ylidene, 1-(2,4,6-trimethylphenyl)-3-(butylnitrile)imidazol-2-ylidene, 1-(2,4,6-trimethylphenyl)-3-(pentylnitrile)...
Synthesis and Properties of Chelating N-Heterocyclic Carbene Rhodium(I) Complexes: Synthetic Experiments in Current Organometallic Chemistry
Jose A. Mata, Macarena Poyatos, and Elena Mas-MarzáJournal of Chemical Education2011 88 (6), 822-824Synthesis and Properties of Chelating N-Heterocyclic Carbene Rhodium(I) Complexes: Synthetic Experiments in Current Organometallic Chemistry
Jose A. Mata, Macarena Poyatos, and Elena Mas-MarzáJournal of Chemical Education2011 88 (6), 822-824The preparation and characterization of two air-stable Rh(I) complexes bearing a chelating N-heterocyclic carbene (NHC) ligand is described. The synthesis involves the preparation of a Ag(I)−NHC complex and its use as carbene transfer agent to a Rh(I) ...
Optimized Syntheses of Cyclopentadienyl Nickel Chloride Compounds Containing N-Heterocyclic Carbene Ligands for Short Laboratory Periods
Jason Cooke and Owen C. LightbodyJournal of Chemical Education2011 88 (1), 88-91Optimized Syntheses of Cyclopentadienyl Nickel Chloride Compounds Containing N-Heterocyclic Carbene Ligands for Short Laboratory Periods
Jason Cooke and Owen C. LightbodyJournal of Chemical Education2011 88 (1), 88-91Experiments are described for the preparation of imidazolium chloride precursors to N-heterocyclic carbenes and their cyclopentadienyl nickel chloride derivatives. The syntheses have been optimized for second- and third-year undergraduate laboratories ...
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- Received: August 03, 2009
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