Synthesis of Benzopyran-Phenylpropanoid Hybrids via Matsuda-Heck-Arylation and Allylic Oxidation

The synthesis of coumarin- and flavonoid-chalcone hybrids via Pd-catalyzed Heck-type coupling of arene diazonium salts and 8-allylcoumarins and -flavonoids is reported. The β-hydride elimination step proceeds with high regioselectivity if an OMOM-substituent is present at the position C7, adjacent t...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2024-12, Vol.89 (24), p.18585
Hauptverfasser: Otte, Fabian, Greese, Julia, Foß, Stefan, Krüger, Mandy, Sperlich, Eric, Kwesiga, George, Schmidt, Bernd
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The synthesis of coumarin- and flavonoid-chalcone hybrids via Pd-catalyzed Heck-type coupling of arene diazonium salts and 8-allylcoumarins and -flavonoids is reported. The β-hydride elimination step proceeds with high regioselectivity if an OMOM-substituent is present at the position C7, adjacent to the allyl group. A selective allylic oxidation of the coupling products was accomplished using DDQ in the presence of silica to furnish the chalcones.
ISSN:1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02520