ArticleJournal of the American Chemical Society2010
Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: a ligand-based strategy to achieve aerobic catalytic turnover.
Article in Journal of the American Chemical Society, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 52 papers.
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Who cites it
52 citing papers in PubMed.
- Advances in Ligand Development for Wacker-Type Oxidation.ACS omega · 2026Review
- C(spJournal of the American Chemical Society · 2025Article
- Copper(II) NHC pincer complexes containing 1,2,3-triazole units: Synthesis, structure and catalysis for C─N bond forming reactions.Tetrahedron letters · 2025Article
- Copper(II)-catalyzed selective reduction of chalcones using phenylsilane.Tetrahedron letters · 2025Article
- Mechanistic Studies of Alkyl Chloride Acetoxylation by Pt-Sb Complexes.Organometallics · 2025Article
- Palladium-Catalyzed Acetoxylation of γ-Dehydro-aryl-himachalene: The Synthesis of a Novel Allylic Acetoxylated Sesquiterpene and a π-Allyl Palladium(II) Complex.Molecules (Basel, Switzerland) · 2024Article
- Tandem dehydrogenation-olefination-decarboxylation of cycloalkyl carboxylic acids via multifold C-H activation.Nature communications · 2024Article
- Overcoming Pd Catalyst Deactivation in the C-H Coupling of Tryptophan Residues in Water Using Air as the Oxidant.ACS catalysis · 2024Article
- Transannular Functionalization of Multiple C(spOrganometallics · 2023Article
- Cu-Catalyzed Chan-Evans-Lam Coupling Reactions of 2-Nitroimidazole with Aryl Boronic Acids: An Effort toward New Bioactive Agents against S. pneumoniae.Chemistry & biodiversity · 2022Article
- Evidence for Charge Delocalization in Diazafluorene Ligands Supporting Low-Valent [Cp*Rh] Complexes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Metal-free allylic C-H nitrogenation, oxygenation, and carbonation of alkenes by thianthrenation.Chemical science · 2022Article
- Late-Stage Diversification: A Motivating Force in Organic Synthesis.Journal of the American Chemical Society · 2021Article
- Benzoquinone Cocatalyst Contributions to DAF/Pd(OAc)ACS catalysis · 2021Article
- Can Donor Ligands Make Pd(OAc)Journal of the American Chemical Society · 2020Article
- 4,5-Diazafluorene and 9,9'-Dimethyl-4,5-Diazafluorene as Ligands Supporting Redox-Active Mn and Ru Complexes.Molecules (Basel, Switzerland) · 2020Article
- Tuning the copper(II)/copper(I) redox potential for more robust copper-catalyzed C-N bond forming reactions.European journal of inorganic chemistry · 2020Article
- Base-Assisted C-H Bond Cleavage in Cross-Coupling: Recent Insights into Mechanism, Speciation, and Cooperativity.Israel journal of chemistry · 2020Article
- Aerobic Acyloxylation of Allylic C-H Bonds Initiated by a PdChemSusChem · 2019Article
- Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C-H Acetoxylation Catalyzed by Pd(OAc)Journal of the American Chemical Society · 2019Article
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4 authors.
Funding
Abstract
Pd-catalyzed C-H oxidation reactions often require the use of oxidants other than O(2). Here we demonstrate a ligand-based strategy to replace benzoquinone with O(2) as the stoichiometric oxidant in Pd-catalyzed allylic C-H acetoxylation. Use of 4,5-diazafluorenone (1) as an ancillary ligand for Pd(OAc)(2) enables terminal alkenes to be converted to linear allylic acetoxylation products in good yields and selectivity under 1 atm O(2). Mechanistic studies have revealed that 1 facilitates C-O reductive elimination from a π-allyl-Pd(II) intermediate, thereby eliminating the requirement for benzoquinone in this key catalytic step.
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