Paria, Suva and Kais, Viktor and Reiser, Oliver (2014) Visible Light-Mediated Coupling of alpha-Bromochalcones with Alkenes. ADVANCED SYNTHESIS & CATALYSIS, 356 (13). pp. 2853-2858. ISSN 1615-4150, 1615-4169
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Photoredox catalyzed intermolecular couplings of alpha-bromochalcones to olefins have been developed. Employing 1 mol% of the iridium complex Ir(ppy)(3) as photocatalyst, vinyl radicals are generated from a-bromochalcones as the key intermediate, which efficiently engage in a formal [4+2] cyclization with various alkenes. The resulting 3,4-dihydronaphthalenes can be readily transformed to the corresponding naphthalenes and further cyclized to 5H-benzo[c]fluorenes. Alternatively, Heck-type coupling products are obtained with sterically more hindered alkenes or allylated products if the alkene possesses a suitable leaving group in the allylic position.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | PHOTOREDOX CATALYSIS; SUBSTITUTED DIHYDRONAPHTHALENES; ORGANOLITHIUM REAGENTS; SYNTHETIC APPLICATIONS; ESTROGEN-RECEPTOR; ORGANIC-SYNTHESIS; C-C; 1,2-DIHYDRONAPHTHALENES; PHOTOCHEMISTRY; CYCLOADDITION; cyclization; dihydronaphthalenes; olefins; vinyl radicals; visible light photocatalysis |
| 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: | 13 Aug 2019 12:56 |
| Last Modified: | 13 Aug 2019 12:56 |
| URI: | https://pred.uni-regensburg.de/id/eprint/9545 |
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