Reichle, Alexander and Koch, Magdalena and Sterzel, Hannes and Grosskopf, Lea-Joy and Floss, Johannes and Rehbein, Julia and Reiser, Oliver (2023) Copper(I) Photocatalyzed Bromonitroalkylation of Olefins: Evidence for Highly Efficient Inner-Sphere Pathways. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 62 (16): e202219086. ISSN 1433-7851, 1521-3773
Full text not available from this repository. (Request a copy)Abstract
We report the visible light-mediated copper-catalyzed vicinal difunctionalization of olefins utilizing bromonitroalkanes as ATRA reagents. This protocol is characterized by high yields and fast reaction times under environmentally benign reaction conditions with exceptional scope, allowing the rapid functionalization of both activated and unactivated olefins. Moreover, late-stage functionnalization of biologically active molecules and upscaling to gram quantities is demonstrated, which offers manifold possibilities for further transformations, e.g. access to nitro- and aminocyclopropanes. Besides the synthetic utility of the title transformation, this study undergirds the exclusive role of copper in photoredox catalysis showing its ability to stabilize and interact with radical intermediates in its coordination sphere. EPR studies suggest that such interactions can even outperform a highly favorable cyclization of transient to persistent radicals contrasting iridium-based photocatalysts.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | TRANSFER RADICAL-ADDITION; PHOTOREDOX CATALYSIS; ALKENES; Copper; Homogeneous Catalysis; Photocatalysis; Radicals; Reaction Mechanism |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 05 Mar 2024 11:35 |
| Last Modified: | 05 Mar 2024 11:35 |
| URI: | https://pred.uni-regensburg.de/id/eprint/59295 |
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