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Müller, Kilian A. ; Nagel, Carolin H. ; Breder, Alexander

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

Müller, Kilian A., Nagel, Carolin H. und Breder, Alexander (2022) Synthesis of 1,3‐Dioxan‐2‐ones by Photo‐Aerobic Selenium‐π‐Acid Multicatalysis. European Journal of Organic Chemistry 26 (2), e202201180.

Veröffentlichungsdatum dieses Volltextes: 17 Jan 2023 08:34
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.53539


Zusammenfassung

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 ...

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.



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Details

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftEuropean Journal of Organic Chemistry
Verlag:WILEY-V C H VERLAG GMBH
Ort der Veröffentlichung:WEINHEIM
Band:26
Nummer des Zeitschriftenheftes oder des Kapitels:2
Seitenbereich:e202201180
Datum29 November 2022
InstitutionenChemie und Pharmazie > Institut für Organische Chemie
Identifikationsnummer
WertTyp
10.1002/ejoc.202201180DOI
Stichwörter / KeywordsCARBON-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
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-535394
Dokumenten-ID53539

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