Highly Efficient Palladium-Catalyzed Boronic Acid Coupling Reactions in Water: Scope and Limitations

J Org Chem. 1997 Oct 17;62(21):7170-7173. doi: 10.1021/jo970439i.

Abstract

The "ligandless" palladium acetate-catalyzed Suzuki cross-coupling reaction of ArX with aryl- and vinylboronic acids in water without organic cosolvent in the presence of tetrabutylammonium bromide is reported. Aryl bromides give high yields and considerably accelerate the coupling. A wide variety of functional groups can be tolerated. Aryl iodides, however, give incomplete conversion and aryl triflate coupling shows no improvement over reported conditions.