Photomediated Solvent-Switched Direct C–H Arylation vs Oxyalkylation of Azauracils Using Unactivated Aryl Iodides
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<sup>2</sup>)-H and C(sp<sup>3</sup>)-H functionalizations. The protocol exhibited broad substrate compatibility and is amenable to scale-up and late-stage functionalization.
Authors
- Amrita Sharma
- Manpreet Kaur
- Raman Kumar
Institutions
- Indian Institute of Technology Roorkee (IN)
- Institute of Organic Synthesis (RU)
- Laboratoire de Synthèse Organique (FR)
- Chemical Synthesis Lab (SG)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-01-09
- DOI
- https://doi.org/10.1021/acs.joc.5c02086
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00