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...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-12, Vol.89 (24), p.18585-18601
Main Authors: Otte, Fabian, Greese, Julia, Foß, Stefan, Krüger, Mandy, Sperlich, Eric, Kwesiga, George, Schmidt, Bernd
Format: Article
Language:English
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Summary: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:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02520