Diastereoselective Aminoacylation of β-Methylstyrenes through Cooperative N-Heterocyclic Carbene and Photoredox Catalysis
Abstract
β-Amino ketones are versatile synthetic intermediates present in numerous biologically active compounds. Herein, we report a diastereoselective aminoacylation of β-methylstyrenes using acyl saccharins as bifunctional reagents to access β-amino ketones through cooperative N-heterocyclic carbene (NHC) and photoredox catalysis. The reaction proceeds via single-electron oxidation of the alkene to generate a radical cation, followed by nucleophilic addition and diastereoselective coupling between the resulting carbon-centered radical and an NHC-bound ketyl radical. This scalable method exhibits broad substrate scope and good functional group tolerance. Mechanistic studies support a radical pathway, and a plausible mechanism for this organocatalytic transformation is proposed.
Fields of Study & Subjects
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 2
- Pages
- 697–703
- Publication date
- 1 January 2026
- Language
- EN