Photocatalytic Decarboxylative Alkylation of Cyclic Imine–BF3 Complexes: A Modular Route to Functionalized Azacycles

Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range of cyclic imine–BF3 complexes to provide α-functionalized azacycles in an operationally simple process. A three-component variant of this transformation incorporating [1...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of the American Chemical Society 2024-09, Vol.146 (38), p.26331-26339
Hauptverfasser: Bhatt, Kamal, Adili, Alafate, Tran, Andrew H., Elmallah, Kamal M., Ghiviriga, Ion, Seidel, Daniel
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Alkyl radicals generated via an acridine photocatalyzed decarboxylation reaction of feedstock carboxylic acids engage with a range of cyclic imine–BF3 complexes to provide α-functionalized azacycles in an operationally simple process. A three-component variant of this transformation incorporating [1.1.1]­propellane as an additional reaction partner enables the synthesis of valuable bicyclopentane (BCP)-containing azacycles. Reactions exhibit good functional group compatibility, enabling late-stage modification of complex bioactive molecules.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.4c08754