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

ABSTRACT: 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.

SUBMITTER: Otte F 

PROVIDER: S-EPMC11667724 | biostudies-literature | 2024 Dec

REPOSITORIES: biostudies-literature