ArticleJournal of the American Chemical Society2020
Palladium-Catalyzed Oxidation of β-C(sp
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 54 citations in OpenAlex.
- Origins of the selectivity of late transition metals of Group 9 and Group 10 for oxidative addition of C-HChemical science · 2026Article
- Palladium-Catalyzed Regio- and Stereoselective C-H Alkynylation of Conjugated Dienols.JACS Au · 2025Article
- A Miniaturized Chemical High Throughput Experimentation Plate to Enable Late-Stage Oxidation Screening and Scale-up.ACS medicinal chemistry letters · 2025Article
- Palladium catalyzed ortho-C(spNature communications · 2024Article
- Ligand-Enabled γ-C(spJournal of the American Chemical Society · 2023Article
- Selective C-H Activation of Unprotected Allylamines by Control of Catalyst Speciation.Chem catalysis · 2023Article
- Ni-catalyzed benzylic β-C(spNature communications · 2022Article
- Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(spChemical reviews · 2021Review
- Article
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
- Chemistry of Tetradentate [ChemistryOpen · 2020Article
- Peptide late-stage C(spChemical science · 2020Article
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
Site-selective functionalizations of C-H bonds are often achieved with a directing group that leads to five- or six-membered metallacyclic intermediates. Analogous reactions that occur through four-membered metallacycles are rare. We report a challenging palladium-catalyzed oxidation of primary C-H bonds β to nitrogen in an imine of an aliphatic amine, a process that occurs through a four-membered palladacyclc intermediate. The success of the reaction relies on the identification, by H/D exchange, of a simple directing group (salicylaldehyde) capable of inducing the formation of this small ring. To gain insight into the steps of the catalytic cycle of this unusual oxidation reaction, a series of mechanistic experiments and density functional theory (DFT) calculations were conducted. The experimental studies showed that cleavage of the C-H bond is rate-limiting and formation of the strained four-membered palladacycle is thermodynamically uphill. DFT calculations corroborated these conclusions and suggested that the presence of an intramolecular hydrogen bond between the oxygen of the directing group and hydroxyl group of the ligating acetic acid is crucial for stabilization of the palladacyclic intermediate.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.