ArticleJournal of the American Chemical Society2012
The discovery of [Ni(NHC)RCN]2 species and their role as cycloaddition catalysts for the formation of pyridines.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- From [NHC─H]Angewandte Chemie (International ed. in English) · 2026Article
- Identifying a Terminal Nickel-Oxygen Complex Bearing an Unsymmetrical β‑Diketiminate Ligand.JACS Au · 2026Article
- Ni-Catalyzed [2 + 2 + 2] Cycloaddition via the Capture of Azametallacyclopentadienes with Allyl Boronate: Facile Access to Fused Pyridine Derivatives.Molecules (Basel, Switzerland) · 2025Article
- Reversible C-CN Bond Cleavage by a Formal Dinickel(I) Hydride Cation.Organometallics · 2024Article
- Multicomponent syntheses of 5- and 6-membered aromatic heterocycles using group 4-8 transition metal catalysts.Chemical science · 2021Review
- Mechanistic Investigations of the Hydrogenolysis of Diaryl Ethers Catalyzed by Nickel Complexes of N-Heterocyclic Carbene Ligands.Journal of the American Chemical Society · 2017Article
- Rational synthesis of normal, abnormal and anionic NHC-gallium alkyl complexes: structural, stability and isomerization insights.Chemical science · 2015Article
- Advances in nickel-catalyzed cycloaddition reactions to construct carbocycles and heterocycles.Accounts of chemical research · 2015Article
- Dimer involvement and origin of crossover in nickel-catalyzed aldehyde-alkyne reductive couplings.Journal of the American Chemical Society · 2014Article
- Mechanistic Evaluation of the Ni(IPr)Organometallics · 2013Article
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4 authors.
Funding
Abstract
The reaction of Ni(COD)(2), IPr, and nitrile affords dimeric [Ni(IPr)RCN](2) in high yields. X-ray analysis revealed these species display simultaneous η(1)- and η(2)-nitrile binding modes. These dimers are catalytically competent in the formation of pyridines from the cycloaddition of diynes and nitriles. Kinetic analysis showed the reaction to be first order in [Ni(IPr)RCN](2), zeroth order in added IPr, zeroth order in nitrile, and zeroth order in diyne. Extensive stoichiometric competition studies were performed, and selective incorporation of the exogenous, not dimer bound, nitrile was observed. Post cycloaddition, the dimeric state was found to be largely preserved. Nitrile and ligand exchange experiments were performed and found to be inoperative in the catalytic cycle. These observations suggest a mechanism whereby the catalyst is activated by partial dimer-opening followed by binding of exogenous nitrile and subsequent oxidative heterocoupling.
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