2024
Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie 2024, 136 DOI: 10.1002/ange.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalystEnantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis
Champlin A, Kwon N, Ellman J. Enantioselective S‐Alkylation of Sulfenamides by Phase‐Transfer Catalysis. Angewandte Chemie International Edition 2024, 63: e202408820. PMID: 39058627, PMCID: PMC11514311, DOI: 10.1002/anie.202408820.Peer-Reviewed Original ResearchExcellent functional group compatibilityChiral sulfur centerFunctional group compatibilityPhase-transfer catalysisEfficient asymmetric synthesisChiral HPLC separationEnantioselective alkylationPseudoenantiomeric catalystsAsymmetric synthesisGroup compatibilityCinchona alkaloidsProtecting groupsSulfur centerPhase-transferReductive cleavageBioactive pharmacophoresAqueous KOHAqueous conditionsHPLC separationBroad scopeSulfenamideCinchonidineSulfiliminePharmacophoreCatalyst
2023
Mechanistic investigation of a Ni-catalyzed electrochemical reductive cleavage of the α-O-4 bond in the lignin model compound benzyl phenyl ether
Lin F, Petrović P, Tse H, Erythropel H, Lam J, Anastas P. Mechanistic investigation of a Ni-catalyzed electrochemical reductive cleavage of the α-O-4 bond in the lignin model compound benzyl phenyl ether. Green Chemistry 2023, 25: 9720-9732. DOI: 10.1039/d3gc01814h.Peer-Reviewed Original ResearchElectrochemical reductive cleavageBenzyl phenyl etherReductive cleavagePhenyl etherO bondReaction mechanismLignin αCarbon paper cathodeO bond scissionCP electrodePaper cathodeRole of methanolElectrode surfaceCatalyst surfaceDFT calculationsProton donorBond scissionRoom temperatureProton transferPhenoxy anionCatalytic cleavageO saltMechanistic routesBenzylic carbonInert atmosphere
2022
Development of a Ni-promoted, selective electrochemical reductive cleavage of the C–O bond in lignin model compound benzyl phenyl ether
Lin F, TSE H, Erythropel H, Petrović P, Garedew M, Chen J, Lam J, Anastas P. Development of a Ni-promoted, selective electrochemical reductive cleavage of the C–O bond in lignin model compound benzyl phenyl ether. Green Chemistry 2022, 24: 6295-6305. DOI: 10.1039/d2gc01510b.Peer-Reviewed Original ResearchBenzyl phenyl etherO bondBenzylic CPhenyl etherElectrochemical protocolElectrochemical reductive cleavageNoble metal catalystsDivalent metal saltsO bond cleavageSubstrate scope studyMetal catalystsCarbon paperUndivided cellBond cleavageMetal saltsRoom temperatureModel compoundsBenzylic ethersNi foamCatalytic hydrogenolysisAmbient pressureReductive cleavageSelective cleavageNi saltsLignin valorization
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