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

Hensinger, Magenta J.; Closs, Anna C.; Trapp, Oliver and Ofial, Armin R. (9. June 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.

• Item Type: Journal article
• EU Funded Grant Agreement Number: 101024710
• EU Projects: 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
• Form of publication: Publisher's Version
• Keywords: organocatalysis, kinetics, prebiotic chemistry, reactivity, linear free energy relationships
• Faculties: Chemistry and Pharmacy; Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1364-548X
• Language: English