2024
Synthesis of α‑Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C–H Bond Addition to 1,3-Dienes and Isocyanates
Yeo J, Tassone J, Ellman J. Synthesis of α‑Quaternary Amides via Cp*Co(III)-Catalyzed Sequential C–H Bond Addition to 1,3-Dienes and Isocyanates. Organic Letters 2024, 26: 9769-9774. PMID: 39481088, PMCID: PMC11578270, DOI: 10.1021/acs.orglett.4c03740.Peer-Reviewed Original Research
2023
Data Science-Enabled Palladium-Catalyzed Enantioselective Aryl-Carbonylation of Sulfonimidamides
van Dijk L, Haas B, Lim N, Clagg K, Dotson J, Treacy S, Piechowicz K, Roytman V, Zhang H, Toste F, Miller S, Gosselin F, Sigman M. Data Science-Enabled Palladium-Catalyzed Enantioselective Aryl-Carbonylation of Sulfonimidamides. Journal Of The American Chemical Society 2023, 145: 20959-20967. PMID: 37656964, DOI: 10.1021/jacs.3c06674.Peer-Reviewed Original ResearchCross-coupling methodsHeteroaryl iodidesLigand descriptorsExcellent yieldsCoupling partnersChemical spaceMedicinal chemistrySulfonimidamidesAgrochemical discoveryVirtual libraryReaction optimizationOptimal conditionsEfficient strategyHeteroarylScience techniquesEnantioselectivityArylCatalystIodideReactionChemistryData science techniquesYieldDescriptorsDiverse set
2022
C–H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity
Brandes DS, Ellman JA. C–H bond activation and sequential addition to two different coupling partners: a versatile approach to molecular complexity. Chemical Society Reviews 2022, 51: 6738-6756. PMID: 35822540, PMCID: PMC9364435, DOI: 10.1039/d2cs00012a.Peer-Reviewed Original ResearchConceptsAddition reactionH bondsMolecular complexityAtom-economical reactionH bond activationH bond additionSingle reaction sequenceBond activationΣ-bondBond additionCarbonyl compoundsΠ bondsΠ-systemType of functionalityStereochemical controlCoupling partnersMild conditionsSubsequent couplingReaction sequenceVersatile approachDifferent coupling partnersReagentsSequential additionMore complex structuresReactionStereoselective Synthesis of Allenyl Alcohols by Cobalt(III)‐Catalyzed Sequential C−H Bond Addition to 1,3‐Enynes and Aldehydes
Xu C, Tassone JP, Mercado BQ, Ellman JA. Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)‐Catalyzed Sequential C−H Bond Addition to 1,3‐Enynes and Aldehydes. Angewandte Chemie International Edition 2022, 61: e202202364. PMID: 35420724, PMCID: PMC9189073, DOI: 10.1002/anie.202202364.Peer-Reviewed Original ResearchConceptsH bond additionBond additionX-ray structural characterizationH bond substratesFirst exampleCoupling partnersSilyl groupStructural characterizationStereoselective synthesisBond substratesCyclization conditionsEnynesAdjacent alcoholsAllenyl alcoholsLarge substituentsHigh stereoselectivityBrook rearrangementAldehydesAlcohol productsCatalyzed SequentialEffective substrateAlkynesAlcoholCobaltacycleSubstituentsStereoselective Synthesis of Allenyl Alcohols by Cobalt(III)‐Catalyzed Sequential C−H Bond Addition to 1,3‐Enynes and Aldehydes
Xu C, Tassone J, Mercado B, Ellman J. Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)‐Catalyzed Sequential C−H Bond Addition to 1,3‐Enynes and Aldehydes. Angewandte Chemie 2022, 134 DOI: 10.1002/ange.202202364.Peer-Reviewed Original ResearchBond additionX-ray structural characterizationFirst exampleCoupling partnersSilyl groupStructural characterizationStereoselective synthesisBond substratesCyclization conditionsAdjacent alcoholsAllenyl alcoholsCo IIIEnynesLarge substituentsHigh stereoselectivityBrook rearrangementAlcohol productsAldehydesCatalyzed SequentialEffective substrateAlkynesAlcoholCobaltacycleSubstituentsAllenes
2018
Selective and synergistic cobalt(iii)-catalysed three-component C–H bond addition to dienes and aldehydes
Boerth JA, Maity S, Williams SK, Mercado BQ, Ellman JA. Selective and synergistic cobalt(iii)-catalysed three-component C–H bond addition to dienes and aldehydes. Nature Catalysis 2018, 1: 673-679. PMID: 30221249, PMCID: PMC6136669, DOI: 10.1038/s41929-018-0123-4.Peer-Reviewed Original ResearchH bond additionBond additionThree-component CCoupling partnersX-ray structural characterizationCarbon-carbon σ-bondsComplex molecular scaffoldsKinetic isotope studiesSynergistic reactivityDrug synthesisWestern fragmentsΣ-bondConvergent synthesisSimple precursorsStereochemical informationLasalocid A.New stereocentresMolecular scaffoldsRapid synthesisNatural productsStructural characterizationHigh regioRelevant moleculesDifferent coupling partnersAldehydes
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
2008
Rh(I)-Catalyzed Arylation of Heterocycles via C−H Bond Activation: Expanded Scope through Mechanistic Insight
Lewis JC, Berman AM, Bergman RG, Ellman JA. Rh(I)-Catalyzed Arylation of Heterocycles via C−H Bond Activation: Expanded Scope through Mechanistic Insight. Journal Of The American Chemical Society 2008, 130: 2493-2500. PMID: 18251465, PMCID: PMC2693036, DOI: 10.1021/ja0748985.Peer-Reviewed Original ResearchConceptsDirect arylationAryl bromide coupling partnerExcellent product yieldsLow molecular weight ligandsFunctional group tolerant methodPurification of reagentsMolecular weight ligandsTetrafluoroborate saltsBond activationProduct isolationAmide solventsAryl bromidesCoupling partnersWeight ligandsMicrowave reactorArylationCatalyzed ArylationHeterocyclesProduct yieldSolventReactionMechanistic insightsRhAzolesCatalyst
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