Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis
An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo-aerobic selenium-π-acid multicatalysis is reported. Until now, conceptually related methods commonly relied either on the stoichiometric addition of electrophiles onto the substrate...
| Published in: | European Journal of Organic Chemistry |
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| Main Authors: | , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Wiley
2022
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| Subjects: | |
| Online Access: | https://epub.uni-regensburg.de/53539/ https://epub.uni-regensburg.de/53539/1/Eur%20J%20Org%20Chem%20-%202022%20-%20M%20ller%20-%20Synthesis%20of%201%203%E2%80%90Dioxan%E2%80%902%E2%80%90ones%20by%20Photo%E2%80%90Aerobic%20Selenium%E2%80%90%20%E2%80%90Acid%20Multicatalysis.pdf https://doi.org/10.1002/ejoc.202201180 https://doi.org/10.5283/epub.53539 |
| Summary: | An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters by means of photo-aerobic selenium-π-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. |
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