Herein, we report the use of the Suzuki-Miyaura cross-coupling reaction for the preparation of a library of synthetic derivatives of flavonoids for biological activity assays. We have investigated the reactivity of halogenated flavonoids with aryl boronates and with boronyl flavonoids. This reaction was used to prepare new synthetic derivatives of flavonoids substituted at C-8 with aryl, heteroaryl, alkyl, and boronate substituents. The formation of flavonoid boronate enabled a cross-coupling reaction with halogenated flavones yielding biflavonoids connected at C-8. This method was used for the preparation of natural compounds including C-8 prenylated compounds, such as sinoflavonoid NB. Flavonoid boronates were used for the preparation of rare C-8 hydroxyflavonoids (natural flavonoids gossypetin and hypolaetin). A series of previously unknown derivatives of quercetin and luteolin were prepared and fully characterized.

• Keywords
• Suzuki–Miyaura cross-coupling reaction, borylation, flavonoids, prenylation,
• MeSH
• Flavonoids chemistry   MeSH
• Catalysis MeSH
• Boronic Acids chemistry   MeSH
• Luteolin chemistry   MeSH
• Molecular Structure MeSH
• Palladium chemistry   MeSH
• Quercetin chemistry   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Flavonoids MeSH
• gossypetin MeSH Browser
• Boronic Acids MeSH
• Luteolin MeSH
• Palladium MeSH
• Quercetin MeSH