Palladium-Catalyzed Stereoselective Difunctionalization of Bicyclic Alkenes with Organoammonium Salts and Organoboronic Compounds.

A palladium-catalyzed difunctionalization of bicyclic alkenes with organoammonium salts and organoboronic compounds was reported. A wide range of functionalized cyclic products, including those bearing functional groups, were produced stereoselectively in good to excellent yields. The gram-scale experiment, one-pot operation, and synthetic application of β-borylated products further demonstrated the synthetic value of this new reaction in organic synthesis.