Easy Access to N,N -Disubstituted 2-Imidazolidinones from Weinreb-Type Amides and Enamides via Visible-Light-Mediated Radical Smiles Rearrangement
Abstract
This paper describes a visible-light-driven photoredox catalytic strategy for the facile preparation of N,N -disubstituted-2-imidazolidinones from Weinreb-type amides (WAs) and N -acyl enamines. The reaction commences with the photoredox-catalyzed heterolysis of the N–O bond in the WAs, generating a nitrogen-centered amidyl radical. This radical subsequently adds to the enamine with high regioselectivity, triggering a tandem process comprising a radical Smiles rearrangement and an intramolecular acyl-retentive cyclization. This cascade ultimately leads to the formation of a highly reconstructed 2-imidazolidinone scaffold. This study presents a novel, straightforward approach to the synthesis of diversely substituted 2-imidazolidinones.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Advanced Synthetic Organic Chemistry
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 17
- Pages
- 5345–5349
- Publication date
- 21 April 2026
- Language
- EN