Ruthenium-Catalyzed C-H Activation of Salicylaldehyde and Decarboxylative Coupling of Alkynoic Acids for the Selective Synthesis of Homoisoflavonoids and Flavones.

Homoisoflavonoids were formed in DMSO exclusively, and flavones were formed in t-AmOH when salicylaldehyde and alkynoic acids reacted with [Ru(p-cymene)Cl2]2 and CsOAc. They were formed through C-H activation of salicylaldehyde and decarboxylative coupling of alkynoic acid. This reaction system showed good yields, broad substrate scope, and good functional group tolerance. It was found that chalcone was an intermediate in the formation of both homoisoflavonoid and flavone.