Mueller, Kilian A. and Nagel, Carolin H. and Breder, Alexander (2023) Synthesis of 1,3-Dioxan-2-ones by Photo-Aerobic Selenium-pi-Acid Multicatalysis. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 26 (2): e202201180. ISSN 1434-193X, 1099-0690
Full text not available from this repository. (Request a copy)Abstract
An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo-aerobic selenium-pi-acid multicatalysis is reported. Until now, conceptually related methods commonly relied either on the stoichiometric addition of electrophiles onto the substrate's alkene moiety or the presence of pre-installed leaving groups in allylic position of said alkene to - in part, catalytically - initiate an intramolecular attack by an adjacent carbonic acid ester group. In sharp contrast, the current study shows that the C-C double bond of homoallylic carbonic acid esters can be directly activated by the catalytic interplay of a pyrylium dye and a diselane using ambient air as the sole oxidant and visible light as an energy source.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CARBON-DIOXIDE; HOMOALLYLIC ALCOHOLS; CYCLIC CARBONATES; STEREOSELECTIVE FUNCTIONALIZATION; DIASTEREOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; STEP ECONOMY; AMINATION; CATALYSTS; CO2; alkenes; allylic oxidation; photoredox catalysis; selenium-pi-acid catalysis; 1,3-dioxan-2-ones |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Feb 2024 10:35 |
| Last Modified: | 20 Feb 2024 10:35 |
| URI: | https://pred.uni-regensburg.de/id/eprint/56878 |
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