Photomediated Solvent-Switched Direct C–H Arylation vs Oxyalkylation of Azauracils Using Unactivated Aryl Iodides
Abstract
Herein, we report a unified, photoinduced, solvent-controlled strategy for two distinct C–H functionalizations of azauracils: arylation in DMSO and oxyalkylation in THF via direct homolytic cleavage of the C–I bond of photoexcited aryl iodides. Mechanistic studies revealed a dual role of aryl iodides, serving as arylating agents in DMSO and hydrogen atom transfer (HAT) mediators with cyclic ethers, thus facilitating divergent C(sp 2 )–H and C(sp 3 )–H functionalizations. The protocol exhibited broad substrate compatibility and is amenable to scale-up and late-stage functionalization.
Fields of Study & Subjects
Radical Photochemical Reactions
Catalytic C–H Functionalization Methods
Oxidative Organic Chemistry Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 3
- Pages
- 1276–1283
- Publication date
- 9 January 2026
- Language
- EN