Visible-Light-Induced Radical Cascade [4 + 2]/[4 + 2] Cycloaddition of Underexplored N -Acryloyl Indoles To Access Dihydropyrido[1,2- a ]-indolones
Abstract
High Resolution Image Download MS PowerPoint Slide We report a visible-light-mediated radical cascade [4 + 2]/[4 + 2] cycloaddition of simple N -acryloyl indoles and N -hydroxyphthalimide esters, which provides a streamlined route to structurally complex dihydropyrido[1,2- a ]-indolones. The reaction features a sequence of four consecutive radical additions involving two N -acryloyl indole molecules, which forges four new C–C bonds and induces dearomatization of one indole ring. The proposed mechanism is supported by observations of [4 + 2] cycloaddition byproducts and additional control experiments. The synthetic utility of this method is demonstrated by the scale-up reaction and downstream derivatizations.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Oxidative Organic Chemistry Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 9
- Pages
- 2852–2858
- Publication date
- 23 February 2026
- Language
- EN