Photoexcited Nitroarenes: A Workhorse for Strategic Synthesis of N -Heterocycles via Reductive C–N Coupling/Cyclization Cascade
Abstract
Owing to their distinct electron-withdrawing properties, a combined nitro-assisted functionalization followed by tandem nitro group manipulation is emerging to streamline pharmaceutical synthesis. Herein, we disclose an expedient protocol for the synthesis of N -heterocycles, such as N -aryl indole, oxindole, benzoxazinone, and (tetrahydro)quinolinone, from photoexcited o -tethered nitroarenes at ambient temperature through a tandem C–N coupling/intramolecular cyclization. A nitrene intermediate is formed to furnish intermolecular C–N coupling with boronic acids, followed by intramolecular cyclization with pendant functional groups in a single operation. This metal-free, cascade annulation reaction is scalable and has been applied to the synthesis of APIs and drugs.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Radical Photochemical Reactions
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 15
- Pages
- 4822–4828
- Publication date
- 1 April 2026
- Language
- EN