Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling.

[reaction--see text] N,N-Bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride with palladium(II) acetate (2 mol %) was used as catalyst, without added base, to efficiently cross couple aryl, vinyl, and alkyl boronates and boronic acids with aryldiazonium tetrafluoroborate substrates. The reactions were performed at 0 degrees C or rt, giving product in 2 to 4 h with 80 to 90% yields for isolated materials. Diazonium ions, formed in situ, also cross couple under these conditions.