Engaging Photoexcited ortho -Substituted Nitroarenes and Aryl/Alkyl Boronic Acids in Reductive C–N Coupling
Abstract
Despite significant progress, metal-free reductive C–N coupling with ortho -substituted nitroarenes and alkyl boronic acids as coupling partners remains unknown. We disclose herein an expedient protocol for the photoinduced, metal-free reductive C–N coupling of these challenging substrates, accessing a series of diarylamine-based and N-alkylated medicinal scaffolds. Remarkably, the alkyl boronic acids, which were inefficient in earlier reports due to sluggish 1,2-migratory aptitude, also furnished excellent yields (up to 98%). In addition, DFT studies show that ortho -substituted nitroarenes require higher energy for n → π* photoexcitation to initiate the reaction, demanding a longer reaction time compared to those of electron-rich nitroarenes. The reaction is scalable and proceeds smoothly under renewable sunlight irradiation.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Catalytic Cross-Coupling Reactions
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 2
- Pages
- 663–668
- Publication date
- 5 January 2026
- Language
- EN