Flavonoids are kinds of natural products with various phenolic structures, isolated from natural sources including fruits, vegetables, tea and their synthetic derivatives. Flavanones, one of flavonoid subgroups, were recently focused on its diverse biological activities such as anti-cancer, anti-oxidative, anti-inflammatory, and anti-mutagenic effects. To date, most of synthetic flavanones are often generated through the Claisen-Schmidt condensation of 2-hydroxyacetophenones with benzaldehydes and the cyclization of resulting chalcone intermediates under the acidic or basic refluxing condition, which is not compatible for acid-/base- labile compounds. Thus, novel synthetic routes towards flavanones have been pursued in the field of medicinal and organic chemistry. Herein, we report a facile and versatile approach to flavanones from readily available chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids <i>via</i> palladium(II)-catalyzed one-pot β-arylation. This method is scalable with easily accessible reagents and provides various flavanones containing wide range of functional groups in high yields (up to 92%) including biologically active natural products such as liquiritigenin dimethyl ether and naringenin trimethyl ether.

Facile synthesis of flavanones <i>via</i> Pd(II)-catalyzed β-arylation of chromanones with arylboronic acids

2019 Fall National Meeting

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Facile synthesis of flavanones via Pd(II)-catalyzed β-arylation of chromanones with arylboronic acids