Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis ...

• Main Authors: Müller, Kilian A., Nagel, Carolin H., Breder, Alexander
• Format: Article in Journal/Newspaper
• Language: unknown
• Published: Universität Regensburg 2022
• Subjects: alkenes · allylicoxidation · photoredoxcatalysis · selenium-π-acidcatalysis · 1,3-dioxan-2-ones; 540 Chemie; Carbonic acid
• Online Access: https://dx.doi.org/10.5283/epub.53539; https://epub.uni-regensburg.de/id/eprint/53539

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. ...