ArticleJournal of the American Chemical Society2016
Aerobic Linear Allylic C-H Amination: Overcoming Benzoquinone Inhibition.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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Who cites it
28 citing papers in PubMed, 166 citations in OpenAlex.
- Cu-Catalyzed Three-Component Carbofunctionalization of 1,3-Dienes.ACS catalysis · 2025Article
- Synergistic solvent-catalyst paradigm for sustainable aerobic allylic C-H functionalization.National science review · 2025Article
- Heterogeneous Fe-N-C Cocatalyst for Hydroquinone Oxidation Enables Aerobic Oxidation of Primary Alcohols to Aldehydes.Angewandte Chemie (International ed. in English) · 2025Article
- Allylic C-H oxygenation of unactivated internal olefins by the Cu/azodiformate catalyst system.Nature communications · 2025Article
- A facile synthesis of α,β-unsaturated imines via palladium-catalyzed dehydrogenation.Nature communications · 2024Article
- Cooperative Cu/azodiformate system-catalyzed allylic C-H amination of unactivated internal alkenes directed by aminoquinoline.Nature communications · 2024Article
- Kinetically-driven reactivity of sulfinylamines enables direct conversion of carboxylic acids to sulfinamides.Chemical science · 2023Article
- Asymmetric intermolecular allylic C-H amination of alkenes with aliphatic amines.Science (New York, N.Y.) · 2022Article
- Decarboxylative Sulfinylation Enables a Direct, Metal-Free Access to Sulfoxides from Carboxylic Acids.Angewandte Chemie (International ed. in English) · 2022Article
- Palladium-catalysed selective oxidative amination of olefins with Lewis basic amines.Nature chemistry · 2022Article
- Iron-Catalyzed Oxidative C-O and C-N Coupling Reactions Using Air as Sole Oxidant.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis.Natural products and bioprospecting · 2022Review
- Efficient Aerobic Oxidation of Organic Molecules by Multistep Electron Transfer.Angewandte Chemie (International ed. in English) · 2021Review
- Computational insights into Ir(iii)-catalyzed allylic C-H amination of terminal alkenes: mechanism, regioselectivity, and catalytic activity.RSC advances · 2021Article
- Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of Amines using a Hybrid Hydroquinone/Cobalt Catalyst as Electron Transfer Mediator.Angewandte Chemie (International ed. in English) · 2021Article
- Article
- Efficient Palladium-Catalyzed Aerobic Oxidative Carbocyclization to Seven-Membered Heterocycles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Can Donor Ligands Make Pd(OAc)Journal of the American Chemical Society · 2020Article
- Efficient Stereoselective Carbocyclization toJournal of the American Chemical Society · 2020Article
- Iron(II)-Catalyzed Biomimetic Aerobic Oxidation of Alcohols.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
An efficient aerobic linear allylic C-H amination reaction is reported under palladium(II)/bis-sulfoxide/Brønsted base catalysis. The reaction operates under preparative, operationally simple conditions (1 equiv of olefin, 1 atm O2 or air) with reduced Pd(II)/bis-sulfoxide catalyst loadings while providing higher turnovers and product yields than systems employing stoichiometric benzoquinone (BQ) as the terminal oxidant. Pd(II)/BQ π-acidic interactions have been invoked in various catalytic processes and are often considered beneficial in promoting reductive functionalizations. When such electrophilic activation for functionalization is not needed, however, BQ at high concentrations may compete with crucial ligand (bis-sulfoxide) binding and inhibit catalysis. Kinetic studies reveal an inverse relationship between the reaction rate and the concentration of BQ, suggesting that BQ is acting as a ligand for Pd(II) which results in an inhibitory effect on catalysis.
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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.