2025
Selective Oxidation of Disparate Functional Groups Mediated by a Common Aspartic Acid-Based Peptide Catalyst Platform
Huth S, Stone E, Miller S. Selective Oxidation of Disparate Functional Groups Mediated by a Common Aspartic Acid-Based Peptide Catalyst Platform. Accounts Of Chemical Research 2025, 58: 2072-2087. PMID: 40530828, DOI: 10.1021/acs.accounts.5c00247.Peer-Reviewed Original ResearchConceptsPeptide catalystsMedicinally relevant moleculesPeptide-based catalystsBaeyer-Villiger oxidationAsp peptidesSynthetic reaction conditionsSynthetically relevant transformationsComplex natural productsNatural productsAsymmetric catalysisCatalyst platformStoichiometric oxidantOxygen atomsSelective oxidationNoncovalent interactionsReaction conditionsBioactive natural productsBioactive analoguesMolecular scaffoldsCatalystFunctional groupsDrug analoguesPeptide sequencesRelevant moleculesDrug molecules
2024
Photoelectrochemical CO2 Reduction to CO Enabled by a Molecular Catalyst Attached to High-Surface-Area Porous Silicon
Jia X, Stewart-Jones E, Alvarez-Hernandez J, Bein G, Dempsey J, Donley C, Hazari N, Houck M, Li M, Mayer J, Nedzbala H, Powers R. Photoelectrochemical CO2 Reduction to CO Enabled by a Molecular Catalyst Attached to High-Surface-Area Porous Silicon. Journal Of The American Chemical Society 2024, 146: 7998-8004. PMID: 38507795, DOI: 10.1021/jacs.3c10837.Peer-Reviewed Original ResearchRe catalystsConversion of CO2 to COCO2 reduction to COPhotoelectrochemical CO2 reductionReduction to COSi-based photoelectrodesCO2 to COHigh-surface-areaOptimal reaction conditionsCatalyst attachmentAcetonitrile solutionPhotoelectrochemical conversionSi photoelectrodesSi photocathodeFaradaic efficiencyCatalytic performanceCyclic voltammogramsReaction conditionsSun illuminationCO2 reductionPhotoelectrodeFTIR spectroscopyCatalystPlanar Si waferSi cathodeSurface hydrophobicity of boron nitride promotes PFOA photocatalytic degradation
Wang B, Chen Y, Samba J, Heck K, Huang X, Lee J, Metz J, Bhati M, Fortner J, Li Q, Westerhoff P, Alvarez P, Senftle T, Wong M. Surface hydrophobicity of boron nitride promotes PFOA photocatalytic degradation. Chemical Engineering Journal 2024, 483: 149134. DOI: 10.1016/j.cej.2024.149134.Peer-Reviewed Original ResearchDensity functional theory calculationsRate law analysisFunctional theory calculationsSurface hydroxyl groupsDegradation ratePhotocatalytic degradationHole reactionsHeterogeneous photocatalysisAnatase TiO2Catalyst surfaceReaction conditionsTheory calculationsSurface hydroxylsContact angle measurementsHydroxyl groupsTiO2Light illuminationExposed surface areaAcidic pH conditionsBoron nitrideSurface hydrophobicitySurface coverageSurface areaElectrostatic attractionNeutral pH
2023
Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie International Edition 2023, 63: e202315701. PMID: 38015869, PMCID: PMC10813656, DOI: 10.1002/anie.202315701.Peer-Reviewed Original ResearchS bond formationOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidSynthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation
Greenwood N, Cerny N, Deziel A, Ellman J. Synthesis of N‐Acylsulfenamides from (Hetero)Aryl Iodides and Boronic Acids by One‐Pot Sulfur‐Arylation and Dealkylation. Angewandte Chemie 2023, 136 DOI: 10.1002/ange.202315701.Peer-Reviewed Original ResearchOne-pot approachBoronic acidsBond formationComplex bioactive compoundsComplex precursorSulfur functionalizationDiverse electrophilesSulfur groupsReaction conditionsDrug apixabanDrug precursorsS-substituentsThermal eliminationReaction inputConcerted eliminationMechanistic studiesBioactive compoundsSynthesisIodideBroad scopePrecursorsFunctionalizationCatalystAcidStyreneMultielectrode electrochemical cell for in situ structural characterization of amorphous thin-film catalysts using high-energy X-ray scattering
Kwon G, Kisslinger K, Hwang S, Wright G, Layne B, Zhong H, Pattammattel A, Lynch J, Kim J, Hu G, Brudvig G, Lee W, Nam C. Multielectrode electrochemical cell for in situ structural characterization of amorphous thin-film catalysts using high-energy X-ray scattering. Journal Of Applied Crystallography 2023, 56: 1392-1402. DOI: 10.1107/s1600576723006933.Peer-Reviewed Original ResearchThin film catalystElectrochemical cellGlassy carbonHigh-energy X-ray scatteringStructural characterizationX-ray scatteringWater oxidation catalystsPorous electrode architectureThree-electrode configurationHigh-energy x-ray scattering techniquesSitu structural characterizationPDF analysisIridium oxide filmsMetal oxide layerPair distribution function techniqueElectrode architectureOxidation catalystX-ray Scattering MeasurementsX-ray scattering techniquesReaction conditionsCatalystElectrochemical potentialAtomic pair distribution function (PDF) techniqueElectrodeDeposition technique
2020
Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α‑Amino C–H Arylation and Epimerization
Walker MM, Koronkiewicz B, Chen S, Houk KN, Mayer JM, Ellman JA. Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α‑Amino C–H Arylation and Epimerization. Journal Of The American Chemical Society 2020, 142: 8194-8202. PMID: 32286827, PMCID: PMC7318553, DOI: 10.1021/jacs.9b13165.Peer-Reviewed Original ResearchConceptsDensity functional theoryH arylation reactionTransient absorption spectroscopyArylation reactionFluorescent spectroscopic methodDiastereomer ratiosΑ-amino CElectron transfer processAbsorption spectroscopyMultiple substitution patternsFunctional theoryDiastereoselective functionalizationRelative energiesSlow epimerizationReaction conditionsSpectroscopic methodsH arylationPure productsGood yieldsSubstitution patternTransfer processObserved distributionHigh diastereoselectivityPiperidine derivativesRadical formation
2019
Modification of a pyridine-alkoxide ligand during the synthesis of coordination compounds
Shopov D, Sharninghausen L, Sinha S, Mercado B, Brudvig G, Crabtree R. Modification of a pyridine-alkoxide ligand during the synthesis of coordination compounds. Inorganica Chimica Acta 2019, 484: 75-78. DOI: 10.1016/j.ica.2018.09.020.Peer-Reviewed Original ResearchPyridine-alkoxide ligandsWater oxidation catalysisHigher oxidation statesCoordination compoundsPincer ligandGeminal methyl groupsCatalytic conditionsOxidation stateOxidation catalystReaction conditionsMinor byproductsAliphatic alkenesMinor productsOxidative conditionsMethyl groupN-oxideLigandsBlue solutionCH groupPincerStructural analoguesSynthesisComplexesCatalystCentral unit
2018
Greener Methodology: An Aldol Condensation of an Unprotected C‑Glycoside with Solid Base Catalysts
de Winter T, Petitjean L, Erythropel H, Moreau M, Hitce J, Coish P, Zimmerman J, Anastas P. Greener Methodology: An Aldol Condensation of an Unprotected C‑Glycoside with Solid Base Catalysts. ACS Sustainable Chemistry & Engineering 2018, 6: 7810-7817. DOI: 10.1021/acssuschemeng.8b00816.Peer-Reviewed Original ResearchSolid base catalystBase catalystC-glycosidesElectron-poor moietiesAldol condensation reactionMultiple reaction parametersCatalytic systemCondensation reactionMgO catalystReaction conditionsExcellent yieldsAromatic aldehydesAldol condensationBulky groupsReaction parametersGreen alternativeCatalystOptimal conditionsRecyclabilityMoietyAldehydesKetonesSynthesisReactionCondensation
2017
Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst
Hurtley AE, Stone EA, Metrano AJ, Miller SJ. Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst. The Journal Of Organic Chemistry 2017, 82: 11326-11336. PMID: 29020446, PMCID: PMC5738245, DOI: 10.1021/acs.joc.7b02339.Peer-Reviewed Original Research
2016
Formate to Oxalate: A Crucial Step for the Conversion of Carbon Dioxide into Multi‐carbon Compounds
Lakkaraju P, Askerka M, Beyer H, Ryan C, Dobbins T, Bennett C, Kaczur J, Batista V. Formate to Oxalate: A Crucial Step for the Conversion of Carbon Dioxide into Multi‐carbon Compounds. ChemCatChem 2016, 8: 3453-3457. DOI: 10.1002/cctc.201600765.Peer-Reviewed Original ResearchMulti-carbon compoundsDensity functional theory calculationsSelective catalytic conversionIndustrial-scale synthesisFunctional theory calculationsChain reaction mechanismCatalytic performanceIon catalystAlkali formateIon catalysisConversion of formateBond formationCatalytic conversionQuantitative conversionIon intermediateReaction conditionsRaman spectroscopyTheory calculationsReaction mechanismCatalytic mechanismSodium hydrideOxalate saltsSodium formateFormateEfficient conversionEster Hydrogenation Catalyzed by CNN-Pincer Complexes of Ruthenium
Kim D, Le L, Drance M, Jensen K, Bogdanovski K, Cervarich T, Barnard M, Pudalov N, Knapp S, Chianese A. Ester Hydrogenation Catalyzed by CNN-Pincer Complexes of Ruthenium. Organometallics 2016, 35: 982-989. DOI: 10.1021/acs.organomet.6b00009.Peer-Reviewed Original ResearchDehydrogenation of primary alcoholsCatalytic turnoverComplexes of rutheniumHydrogenation of estersMethyl esterEster hydrogenationRuthenium complexesLigand structureReaction conditionsInactive catalystsMild conditionsBenzyl alcoholPrimary alcoholsReaction mixtureHydrogenReverse reactionLigandEsterCatalystDehydrogenationBase-catalyzed transesterificationBenzylRutheniumReactionHexyl ester
2014
Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation.
Abascal NC, Lichtor PA, Giuliano MW, Miller SJ. Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation. Chemical Science 2014, 5: 4504-4511. PMID: 25386335, PMCID: PMC4224318, DOI: 10.1039/c4sc01440e.Peer-Reviewed Original Research
2013
The Roles of Counterion and Water in a Stereoselective Cysteine‐Catalyzed Rauhut–Currier Reaction: A Challenge for Computational Chemistry
Osuna S, Dermenci A, Miller SJ, Houk KN. The Roles of Counterion and Water in a Stereoselective Cysteine‐Catalyzed Rauhut–Currier Reaction: A Challenge for Computational Chemistry. Chemistry - A European Journal 2013, 19: 14245-14253. PMID: 24038400, PMCID: PMC3918516, DOI: 10.1002/chem.201300745.Peer-Reviewed Original ResearchConceptsRauhut-Currier reactionCysteine derivativesComplete reaction pathwayRole of counterionsPresence of counterionsRate-determining eliminationMichael addition productsDensity functional theoryComputational chemistryExplicit water solvationWater solvationPotassium counterionsReaction conditionsReaction pathwaysAddition productsEnantiomer pairsThiol catalystCatalyst eliminationPossible stereoisomersCurrier ReactionFunctional theoryCounterionsNucleophilesReactionDerivatives
2012
Synthesis and computational studies of Mg complexes supported by 2,2′:6,2′′-terpyridine ligands
Guard LM, Palma JL, Stratton WP, Allen LJ, Brudvig GW, Crabtree RH, Batista VS, Hazari N. Synthesis and computational studies of Mg complexes supported by 2,2′:6,2′′-terpyridine ligands. Dalton Transactions 2012, 41: 8098-8110. PMID: 22430933, DOI: 10.1039/c2dt12426b.Peer-Reviewed Original ResearchGrignard reagentsTerpyridine ligandTridentate nitrogen ligandsDiethyl etherX-ray crystallographyDialkyl speciesTerpy ligandFree terpyridinesNitrogen ligandsAlkyl complexesAlkyl speciesCoordination planeNitrogen donorsDFT studySteric bulkTerpyridineCompounds 5aReaction conditionsMg complexesSimilar reactionComputational studyOnly productLigandsMixed halidesReagents
2011
Linear and cyclic C -glycosides as surfactants
Foley P, Phimphachanh A, Beach E, Zimmerman J, Anastas P. Linear and cyclic C -glycosides as surfactants. Green Chemistry 2011, 13: 321-325. DOI: 10.1039/c0gc00407c.Peer-Reviewed Original ResearchCarbohydrate-based surfactantsAlkyl aldehydesC bond formationGlycosidic linkagesFacile synthesisBond formationReaction conditionsSurfactant propertiesGood yieldsSurfactantsAdditional analoguesRenewable feedstockC-glycosidesCarbohydrate CAldehydesMost carbohydratesNew classDesirable performance propertiesPerformance propertiesChemistryPyrrolidineRecent advancesPropertiesSynthesisStoichiometry
2009
Application of Daugulis Copper-Catalyzed Direct Arylation to the Synthesis of 5-Aryl Benzotriazepines
Yotphan S, Bergman RG, Ellman JA. Application of Daugulis Copper-Catalyzed Direct Arylation to the Synthesis of 5-Aryl Benzotriazepines. Organic Letters 2009, 11: 1511-1514. PMID: 19260648, PMCID: PMC2674648, DOI: 10.1021/ol900103a.Peer-Reviewed Original Research
2006
Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates
Schneekloth J, Pucheault M, Crews C. Construction of Highly Substituted Stereodefined Dienes by Cross‐Coupling of α‐Allenic Acetates. European Journal Of Organic Chemistry 2006, 2007: 40-43. DOI: 10.1002/ejoc.200600721.Peer-Reviewed Original ResearchNatural product chemistryStraightforward reaction conditionsOrganic chemistryProduct chemistryOrganozinc reagentsSubstrate scopeReaction conditionsPalladium precatalystsHigh selectivityZ selectivityCross couplingSelectivityChemistryReactionLigandsDieneInteresting reversalPrecatalystOlefinsReagentsProductsAcetateAssemblyBroad useAppropriate choice
2005
Catalytic Enantioselective Sulfinyl Transfer Using Cinchona Alkaloid Catalysts
Peltier HM, Evans JW, Ellman JA. Catalytic Enantioselective Sulfinyl Transfer Using Cinchona Alkaloid Catalysts. Organic Letters 2005, 7: 1733-1736. PMID: 15844893, DOI: 10.1021/ol050275p.Peer-Reviewed Original ResearchConceptsCinchona alkaloid catalystsCatalytic Enantioselective SynthesisPractical reaction conditionsAvailable cinchona alkaloidsSuperior catalystTransfer reactionsReaction conditionsSulfinate estersEnantioselective synthesisCinchona alkaloidsBenzyl alcoholEster productsCatalystAlcoholSynthesisTransferReactionChlorideEstersEEAlkaloidsYieldProducts
2003
Improved Synthesis of tert-Butanesulfinamide Suitable for Large-Scale Production
Weix DJ, Ellman JA. Improved Synthesis of tert-Butanesulfinamide Suitable for Large-Scale Production. Organic Letters 2003, 5: 1317-1320. PMID: 12688748, DOI: 10.1021/ol034254b.Peer-Reviewed Original ResearchCatalytic asymmetric oxidationHomogeneous reaction conditionsChiral ligandsAsymmetric oxidationImproved synthesisReaction conditionsDi-tertButyl disulfidePrevious synthesesSolvent acetoneLarge-scale productionSingle stepSynthesisKey stepM concentrationLigandsOxidationAcetoneDisulfideReactionStepMaterials
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