Application of the Suzuki-Miyaura Reaction in the Synthesis of Flavonoids

Abstract

The application of the Suzuki-Miyaura reaction in the synthesis of flavonoids, an important class of natural products, is reviewed. This reaction has not only been employed to provide access to flavonoid nuclei, but has also been applied to the synthesis of dimeric flavonoids and in the synthesis of libraries of flavonoid derivatives for biological activity studies. The classes of flavonoids that are discussed are the chalcones, flavones, isoflavones, neoflavones, biflavones and derivatives of flavonoids obtained by C-C bond formation via the Suzuki-Miyaura reaction.

Nickel N-heterocyclic carbene complexes and their utility in homogeneous catalysis

“…Suzuki [243] reaction is a palladium catalyzed C-C cross coupling reaction between aryl boronic acids and aryl halides in the presence of a base and is counted among the top few popular methods available for the construction of carbon-carbon bonds in the organic synthesis these days [244]. Though a large number of the palladium complexes [245] including those of the N-heterocyclic carbene ones [246] are routinely used as precatalysts for the Suzuki coupling reactions, similar reports of successful nickel Nheterocyclic carbene catalysts for the coupling reaction have been comparatively rare (Scheme 17) [247].…”

Efficient Synthesis of Eriodictyol from l -Tyrosine in Escherichia coli

“…Chemical synthesis is associated with toxic by-products and requires extreme reaction conditions, as in the application of the Suzuki-Miyaura reaction (11). Therefore, chemical synthesis is not suitable for the production of flavonoids to be incorporated into food ingredients or cosmetics.…”

Ionic Liquids and Ohmic Heating in Combination for Pd-Catalyzed Cross-Coupling Reactions: Sustainable Synthesis of Flavonoids

“…The catalyst loading can be further decreased to 0.05 mol%; under such conditions, isoflavone 3a was formed in a 90% yield (Table 1, entry 9). most frequently used methodology [28]. In this regard, ΩH-enhanced cross-coupling reactions, and especially Suzuki-Miyaura reactions, have proven particularly useful for the synthesis of pharmacologically relevant scaffolds [29,30].…”

“…Due to their biological profile, numerous approaches have been reported for the synthesis of flavonoid derivatives. Among them, palladium-catalyzed cross-coupling reactions are gaining much recent interest [21][22][23][24][25][26][27], the Suzuki-Miyaura coupling reaction being the most frequently used methodology [28]. In this regard, ΩH-enhanced cross-coupling reactions, and especially Suzuki-Miyaura reactions, have proven particularly useful for the synthesis of pharmacologically relevant scaffolds [29,30].…”