Carboxylate-Assisted Palladium-Catalyzed Regio- and Stereoselective Mizoroki-Heck Arylation of β-Cyclohexadienyl Acrylates and Styrenes

A carboxylate-assisted palladium-catalyzed Mizoroki-Heck arylation of electron-deficient internal alkenes is described herein. This protocol utilized a free carboxylic acid as the directing group for regio- and stereoselective Mizoroki-Heck arylation of beta-cyclohexadienyl acrylates and styrenes with various aryl iodides. The synthetic application has been exhibited by decarboxylative aromatization and iodolactonization/hydrolysis of the resulting polyenes providing trisubstituted alkenes and structurally diverse hydroxyl lactones. Additionally, mechanistic studies have been performed to elucidate the reaction outcome of regio- and stereoselectivity.

Automated summary

A carboxylate-assisted palladium-catalyzed Mizoroki-Heck arylation of electron-deficient internal alkenes was developed, utilizing free carboxylic acid as a directing group. The synthetic application demonstrated the potential of this method in decarboxylative aromatization and iodolactonization reactions.