Direkt zum Inhalt

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. and 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.

Date of publication of this fulltext: 17 Jan 2023 08:34
Article
DOI to cite this document: 10.5283/epub.53539


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 ...

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.



Involved Institutions


Details

Item typeArticle
Journal or Publication TitleEuropean Journal of Organic Chemistry
Publisher:WILEY-V C H VERLAG GMBH
Place of Publication:WEINHEIM
Volume:26
Number of Issue or Book Chapter:2
Page Range:e202201180
Date29 November 2022
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie
Identification Number
ValueType
10.1002/ejoc.202201180DOI
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 Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-535394
Item ID53539

Export bibliographical data

Owner only: item control page

nach oben