ArticleJournal of the American Chemical Society2014
Dimer involvement and origin of crossover in nickel-catalyzed aldehyde-alkyne reductive couplings.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Distinguishing Competing Mechanistic Manifolds for C(acyl)-N Functionalization by a Ni/JACS Au · 2023Article
- Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.Chemical reviews · 2020Review
- Metal-Free Synthesis of Functionalized Tetrasubstituted Alkenes by Three-Component Reaction of Alkynes, Iodine, and Sodium Sulfinates.ACS omega · 2018Article
- Nickel-catalyzed trifluoromethylthiolation of CspChemical science · 2016Article
- Mechanistic Basis for Regioselection and Regiodivergence in Nickel-Catalyzed Reductive Couplings.Accounts of chemical research · 2015Article
- Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.Journal of the American Chemical Society · 2015Article
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Authors and funding
6 authors.
Funding
Abstract
The mechanism of nickel(0)-catalyzed reductive coupling of aldehydes and alkynes has been studied. Extensive double-labeling crossover studies have been conducted. While previous studies illustrated that phosphine- and N-heterocyclic carbene-derived catalysts exhibited differing behavior, the origin of these effects has now been evaluated in detail. Many variables, including ligand class, sterics of the ligand and alkyne, temperature, and ring size being formed in intramolecular versions, all influence the extent of crossover observed. A computational evaluation of these effects suggests that dimerization of a key metallacyclic intermediate provides the origin of crossover. Protocols that proceed with crossover are typically less efficient than those without crossover given the thermodynamic stability and low reactivity of the dimeric metallacycles involved in crossover pathways.
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