ArticleJournal of the American Chemical Society2013
Aerobic dehydrogenation of cyclohexanone to cyclohexenone catalyzed by Pd(DMSO)2(TFA)2: evidence for ligand-controlled chemoselectivity.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 179 citations in OpenAlex.
- Synthesis of Chiral Carbocycles via Enantioselective β,γ-Dehydrogenation.Nature synthesis · 2024Article
- Tandem dehydrogenation-olefination-decarboxylation of cycloalkyl carboxylic acids via multifold C-H activation.Nature communications · 2024Article
- Article
- Dehydrogenation and Transfer Hydrogenation of Alkenones to Phenols and Ketones on Carbon-Supported Noble Metals.ACS catalysis · 2024Article
- (NHC)Pd(II) hydride-catalyzed dehydroaromatization by olefin chain-walking isomerization and transfer-dehydrogenation.Nature communications · 2022Article
- Selective desaturation of amides: a direct approach to enamides.Chemical science · 2022Article
- C-H Bond Activation Mechanism by a Pd(II)-(μ-O)-Au(0) Structure Unique to Heterogeneous Catalysts.JACS Au · 2022Article
- Mechanism of the Arene-Limited Nondirected C-H Activation of Arenes with Palladium*.Angewandte Chemie (International ed. in English) · 2021Article
- Dehydrogenative Pd and Ni Catalysis for Total Synthesis.Accounts of chemical research · 2021Review
- Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand.Tetrahedron · 2019Article
- β-Selective Aroylation of Activated Alkenes by Photoredox Catalysis.Angewandte Chemie (International ed. in English) · 2019Article
- Allyl-Nickel Catalysis Enables Carbonyl Dehydrogenation and Oxidative Cycloalkenylation of Ketones.Journal of the American Chemical Society · 2019Article
- Chemoselective α,β-Dehydrogenation of Saturated Amides.Angewandte Chemie (International ed. in English) · 2019Article
- Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO.Nature communications · 2018Article
- Metal Catalysts for Heterogeneous Catalysis: From Single Atoms to Nanoclusters and Nanoparticles.Chemical reviews · 2018Article
- Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation.Organic letters · 2018Article
- Auto-Tandem Catalysis: PdChemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Palladium-Catalyzed Aerobic Dehydrogenation of Cyclic Hydrocarbons for the Synthesis of Substituted Aromatics and Other Unsaturated Products.ACS catalysis · 2016Article
- Intramolecular Hydrogen Transfer Reactions Catalyzed by Pentamethylcyclopentadienyl Rhodium and Cobalt Olefin Complexes: Mechanistic Studies.Polyhedron · 2016Article
- Palladium-catalyzed direct β-arylation of ketones with diaryliodonium salts: a stoichiometric heavy metal-free and user-friendly approach.Chemical science · 2015Article
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3 authors at 1 institution in 1 country.
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Abstract
The dehydrogenation of cyclohexanones affords cyclohexenones or phenols via removal of 1 or 2 equiv of H2, respectively. We recently reported several Pd(II) catalyst systems that effect aerobic dehydrogenation of cyclohexanones with different product selectivities. Pd(DMSO)2(TFA)2 is unique in its high chemoselectivity for the conversion of cyclohexanones to cyclohexenones, without promoting subsequent dehydrogenation of cyclohexenones to phenols. Kinetic and mechanistic studies of these reactions reveal the key role of the dimethylsulfoxide (DMSO) ligand in controlling this chemoselectivity. DMSO has minimal kinetic influence on the rate of Pd(TFA)2-catalyzed dehydrogenation of cyclohexanone to cyclohexenone, while it strongly inhibits the second dehydrogenation step, conversion of cyclohexenone to phenol. These contrasting kinetic effects of DMSO provide the basis for chemoselective formation of cyclohexenones.
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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.