Pd/amine catalytic systems for the Suzuki coupling reactions of aryl bromides and arylboronic acids under mild conditions: Monoamines vs. diamines

ORGN 556

Bin Tao, btao@gsu.edu and David W. Boykin, dboykin@gsu.edu. Department of Chemistry, Georgia State University, Atlanta, GA 30303
The palladium-catalyzed Suzuki coupling reaction is a powerful and versatile method to prepare polyaryl compounds. There is a great demand for efficient catalystic systems with simple ligands that provide convenient, economical and practical methods for synthesizing polyaryl compounds.

We have recently reported an effective Pd/amine catalytic system for the Suzuki coupling reaction of aryl bromides and aryl boronic acids in good to excellent yields with a great degree of functional group tolerance under mild conditions. Now, we present the results of the catalytic systems involving a wide range of commercially available simple monoamines and diamines. The results indicate that both the bulkiness and chelating effect of the amines play a significant role for the catalytic activity. Both ethylenediamine/Pd and Cy2NH/Pd are general and efficient catalytic systems for the coupling reaction under mild conditions. Furthermore, these new catalytic systems provide simple and economical improvements to conventional Suzuki coupling catalytic systems.