2024
C–H Activation and Sequential Addition to Dienes and Imines: Synthesis of Amines with β‑Quaternary Centers and Mechanistic Studies on the Complex Interplay Between the Catalyst and Three Reactants
Goodner R, Brandes D, Morais G, Tao Q, Tassone J, Mercado B, Chen S, Ellman J. C–H Activation and Sequential Addition to Dienes and Imines: Synthesis of Amines with β‑Quaternary Centers and Mechanistic Studies on the Complex Interplay Between the Catalyst and Three Reactants. ACS Catalysis 2024, 18124-18133. DOI: 10.1021/acscatal.4c05866.Peer-Reviewed Original ResearchRhodacycle intermediateCatalytic cycleX-ray structure analysisDensity functional theory calculationsC-H activationDeuterium labeling studiesSynthesis of aminesTransition state structuresFunctional theory calculationsFormaldimine precursorsEthyl glyoxylateHigh diastereoselectivityN-CbzNitrogen substituentQuaternary centerAlkyl substituentsAlkyl sulfonamidesC-HTheory calculationsRhodacycleState structuresCarbon sitesDienesX-rayMechanistic studies
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 scopePrecursorsFunctionalizationCatalystAcidStyrene