期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 26, 期 2, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202201180
关键词
alkenes; allylic oxidation; photoredox catalysis; selenium-pi-acid catalysis; 1,3-dioxan-2-ones
An expedient method for the synthesis of cyclic carbonates from homoallylic carbonic acid esters using photo-aerobic selenium-pi-acid multicatalysis is reported. This method directly activates the C-C double bond of homoallylic carbonic acid esters using a pyrylium dye and a diselane, with ambient air as the sole oxidant and visible light as an energy source, without relying on stoichiometric addition of electrophiles or pre-installed leaving groups.
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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