Construction of 3‑Oxazolin-5-one via Visible Light-Induced Nondecarboxylative Coupling and Sequential Reactions
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....
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Veröffentlicht in: | Organic letters 2023-03, Vol.25 (12), p.2098-2102 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | 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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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.3c00469 |