Base-Promoted Denitrogenative Coupling of Nonactive 1,2,3-Triazoles with Ketones: Stereospecific Access to ( Z )-β-Enaminones
Abstract
A base-promoted denitrogenative coupling of nonactive N (1)-aryl-1,2,3-triazoles with nucleophiles of ketones was developed, enabling the assembly of ( Z )-β-enaminones at ambient temperature with complete stereoselectivity. Mechanistic studies indicate that the transformation proceeds through denitrogenative ring opening of the triazole to generate a ketenimine intermediate, followed by nucleophilic addition of the α-carbanion of the ketone generated in situ . This process affords a highly efficient and straightforward means to construct functionalized ( Z )-β-enaminones with a broad substrate scope and excellent yields, by employing readily available N (1)-aryl-1,2,3-triazoles and ketones as starting materials.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Click Chemistry and Applications
Synthesis and Characterization of Pyrroles
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 11
- Pages
- 3406–3411
- Publication date
- 5 March 2026
- Language
- EN