Construction of 3-Oxazolin-5-one via Visible Light-Induced Nondecarboxylative Coupling and Sequential Reactions
Shanshan Ma1, Haoying Cao1, Rongwan Gao2
1College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.
Abstract:
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.
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