Sardana, Sunaina and Pattanaik, Aryaman and Rehbein, Julia and Reiser, Oliver (2025) Copper(II)-Photocatalyzed Radical Anellation of Nitroalkanes with Alkenes or Alkynes for the Synthesis of Isoxazolines and Isoxazoles. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 64 (37). ISSN 1433-7851, 1521-3773
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The visible light-mediated copper(II)-catalyzed one-step synthesis of isoxazolines and isoxazoles from readily available ethyl nitroacetate or phenyl nitromethane is reported. The developed protocol eliminates the need for substrate preactivation or additives, and offers an extensive scope of activated and unactivated alkenes and alkynes as coupling partners. Key intermediates for this formal [3 + 2]-cycloaddition are alpha-nitro radicals generated via photoinduced single-electron oxidation of nitronates, contrasting the generation of such radicals via Cu(I)-photocatalysis by a reductive pathway, which shows a different reaction pattern in the coupling with alkenes.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | MOLECULAR-ORBITAL METHODS; 3+2 CYCLOADDITION; BASIS-SETS; CONDENSATION; ANNULATION; REACTIVITY; OXIMES; OXIDES; Anellation; Cu photocatalysis; Heterocycles; Radical pathway; alpha-nitro radicals |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 27 Aug 2026 07:14 |
| Last Modified: | 27 Aug 2026 07:14 |
| URI: | https://pred.uni-regensburg.de/id/eprint/66147 |
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