Palladium−Imidazolium Carbene Catalyzed Mizoroki−Heck Coupling with Aryl Diazonium Ions

Catalyst formed from N,N-bis(2,6-diisopropylphenyl)dihydroimidazolium chloride and palladium(II) acetate (2 mol %) was used, without added base, to efficiently produce Heck coupled products with olefins and aryl diazonium tetrafluoroborate substrates. The reactions were performed at room temperature, giving product in 2−4 h with 80−90% yields for isolated materials. Diazonium ions, formed in situ directly from anilines, also couple under these conditions.