Cinchona-Based Hydrogen-Bond Donor Organocatalyst Metal Complexes: Asymmetric Catalysis and Structure Determination.
Sándor NagyDóra RichterGyula DargóBalázs OrbánGergő GémesTibor HöltzlZsófia GarádiZsuzsanna FehérJózsef KupaiPublished in: ChemistryOpen (2024)
In this study, we describe the synthesis of cinchona (thio)squaramide and a novel cinchona thiourea organocatalyst. These catalysts were employed in pharmaceutically relevant catalytic asymmetric reactions, such as Michael, Friedel-Crafts, and A 3 coupling reactions, in combination with Ag(I), Cu(II), and Ni(II) salts. We identified several organocatalyst-metal salt combinations that led to a significant increase in both yield and enantioselectivity. To gain insight into the active catalyst species, we prepared organocatalyst-metal complexes and characterized them using HRMS, NMR spectroscopy, and quantum chemical calculations (B3LYP-D4/def2-TZVP), which allowed us to establish a structure-activity relationship.
Keyphrases
- metal organic framework
- highly efficient
- structure activity relationship
- visible light
- molecular dynamics
- ionic liquid
- room temperature
- transition metal
- density functional theory
- solid state
- molecular dynamics simulations
- solid phase extraction
- reduced graphene oxide
- mass spectrometry
- gold nanoparticles
- high resolution mass spectrometry
- gas chromatography