2024
Carbocation Mechanism Revelation of Molecular Iodine-Mediated Dehydrogenative Aromatization of Substituted Cyclic Ketones to Phenols
Jin Y, Petrovic P, Huang S, Banerjee S, Nandy A, Anastas P, Lam J. Carbocation Mechanism Revelation of Molecular Iodine-Mediated Dehydrogenative Aromatization of Substituted Cyclic Ketones to Phenols. The Journal Of Organic Chemistry 2024, 89: 3226-3237. PMID: 38361498, DOI: 10.1021/acs.joc.3c02691.Peer-Reviewed Original ResearchDehydrogenative aromatizationCyclic ketonesDesorption electrospray ionization-mass spectrometryC-H bond activationElectrospray ionization-mass spectrometrySubstrate scope studyUnsaturated cyclic ketonesIonization-mass spectrometryHigh energy barrierProton nuclear magnetic resonanceMass spectrometric analysisBond activationSubstrate scopeDFT calculationsNuclear magnetic resonanceProduct selectivityPhenol etherReaction mechanismCarbocationProduct distributionSpectrometric analysisKetonesWater boiling temperatureAmbient conditionsAromatic precursorsDehydrogenation and Transfer Hydrogenation of Alkenones to Phenols and Ketones on Carbon-Supported Noble Metals
Li K, Kelly H, Franco A, Batista V, Baráth E. Dehydrogenation and Transfer Hydrogenation of Alkenones to Phenols and Ketones on Carbon-Supported Noble Metals. ACS Catalysis 2024, 14: 2883-2896. PMID: 38449532, PMCID: PMC10913045, DOI: 10.1021/acscatal.3c04849.Peer-Reviewed Original ResearchKeto-enol tautomerismCatalytic materialsPresence of hydrogen donorsSelection of catalytic materialsSaturated cyclic ketonesM-O bondsNoble metal catalystsBond distance changesAromatic compoundsEntropy of activationBalance of enthalpyTransfer hydrogenationCyclic ketonesMetal catalystsCatalytic dehydrogenationDienolate intermediateDehydrogenation reactionM-OCyclic alcoholsNoble metalsCatalytic activityHydrogen donorBinding orientationEnonesTautomerism
2014
Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones
Romney DK, Colvin SM, Miller SJ. Catalyst Control over Regio- and Enantioselectivity in Baeyer–Villiger Oxidations of Functionalized Ketones. Journal Of The American Chemical Society 2014, 136: 14019-14022. PMID: 25250713, PMCID: PMC4195385, DOI: 10.1021/ja508757g.Peer-Reviewed Original ResearchConceptsBaeyer-Villiger oxidationPeptide-based catalystsHydrogen bonding interactionsTypes of selectivityParallel kinetic resolutionCatalyst controlFunctionalized KetonesCyclic ketonesFunctional groupsNatural productsComplex moleculesKinetic resolutionAsymmetric processEnantioselectivityRegioKetonesOxidationBroad utilityCatalystCatalysisSelectivityAmidesSynthesisMoleculesProducts
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