Construction of 3-Oxazolin-5-one via Visible Light-Induced Nondecarboxylative Coupling and Sequential Reactions.
Shanshan MaHaoying CaoRongwan GaoYanhong FengYawen GuoWei GuanXin-Fang DuanPeng JiaoPublished in: Organic letters (2023)
3-Oxazolin-5-ones are precursors of nitrile ylides and represent valuable 1,3-dipoles for constructing cyclic imines or pyrrole compounds. Harnessing the power of photocatalysis, we accomplished a straightforward synthesis of 3-oxazolin-5-ones from redox-active esters and secondary nitro compounds. Visible light-induced nondecarboxylative coupling of a redox-active ester, nitro aldol condensation, and subsequent visible light-induced N -oxide deoxygenation were accomplished within 2 h. The reaction mechanism was supported by experimental data and DFT calculations.