The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones

Hensinger, Magenta J.; Closs, Anna C.; Trapp, Oliver und Ofial, Armin R. (9. Juni 2023): The effect of S-alkylation on organocatalytic enamine activation through imidazolidine-4-thiones. In: Chemical Communications

Abstract

Imidazolidine-4-thiones have been suggested as potential prebiotic organocatalysts for light-driven α-alkylations of aldehydes by bromoacetonitrile. However, imidazolidine-4-thiones react with bromoacetonitrile to give S-cyanomethylated dihydroimidazoles. Kinetic studies show that enamines derived from these cyclic secondary amines and aldehydes are more nucleophilic than enamines derived from aldehydes and MacMillan organocatalysts.

• Dokumententyp: Zeitschriftenartikel
• EU Funded Grant Agreement Number: 101024710
• EU-Projekte: Horizon 2020 ; Horizon 2020 > Marie Skłodowska Curie Actions ; Horizon 2020 > Marie Skłodowska Curie Actions > Marie Skłodowska-Curie Individual Fellowships ; Horizon 2020 > Marie Skłodowska Curie Actions > Marie Skłodowska-Curie Individual Fellowships > 101024710: SImCat - Imidazolidinethiones: Underexplored organocatalysts that show promise in catalyzing prebiotic and modern organic reactions
• Publikationsform: Publisher's Version
• Keywords: organocatalysis, kinetics, prebiotic chemistry, reactivity, linear free energy relationships
• Fakultät: Chemie und Pharmazie ; Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1364-548X
• Sprache: Englisch