Katta, Narenderreddy and Zhao, Quan-Qing and Mandal, Tirtha and Reiser, Oliver (2022) Divergent and Synergistic Photocatalysis: Hydro- and Oxoalkylation of Vinyl Arenes for the Stereoselective Synthesis of Cyclopentanols via a Formal [4+1]-Annulation of 1,3-Dicarbonyls. ACS CATALYSIS, 12 (22). pp. 14398-14407. ISSN 2155-5435,
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The controllable divergent reactivity of 1,3-dicarbonyls is described, which enables the efficient hydro-and oxoalkylation of vinyl arenes. Both reaction pathways are initiated through the formation of polarity-reversed C-centered-radical intermediates at the active methylene center of 1,3-dicarbonyls via direct photocatalytic C-H bond transformations. The oxoalkylation of alkenes is achieved under aerobic conditions via a Cu(II)-photomediated rebound mechanism, while the corresponding hydroalkylation becomes possible under a nitrogen atmosphere by the combination of 4CzIPN and a Bronsted base. The breadth of these divergent protocols is demonstrated in the late-stage modification of drugs and natural products and by the transformation of the products to a variety of heterocycles such as pyridines, pyrroles, or furans. Moreover, the two catalytic modes can be combined synergistically for the stereoselective construction of cyclopentanol derivatives in a formal [4+1]-annulation process.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | LIGHT PHOTOREDOX CATALYSIS; FLUOROPHORES; DONOR; cyclopentanol process; cyclopentanols; divergent synthesis; enolate oxidation; photoredox catalysis; synergistic catalysis; visible-light-induced homolysis |
| 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: | 07 Nov 2023 14:10 |
| Last Modified: | 07 Nov 2023 14:10 |
| URI: | https://pred.uni-regensburg.de/id/eprint/56713 |
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