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

• Published in: European Journal of Organic Chemistry
• Main Authors: Müller, Kilian A., Nagel, Carolin H., Breder, Alexander
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2022
• Subjects: 540 Chemie; ddc:540; Carbonic acid
• 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

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.