Catalytic Hydroboration of Organic Nitriles Promoted by Aluminum Complex

We demonstrate an efficient protocol for the chemoselective hydroboration of organic nitriles with pinacolborane (HBpin) and catecholborane (HBcat) using aluminum alkyl complex [kappa(2)-{2-F-C6H4NP(Se)Ph-2}(2)Al-(Me)] as a pre-catalyst to afford diboryl amines under solvent-free and mild conditions (60 degrees C) in high yield. The aluminum complex was prepared by the reaction of [2-F-C6H4NHP(Se)Ph-2] and trimethylaluminum in toluene. The solid-state structure of Al complex is established. Nitriles with a wide array of electron-withdrawing and electron-donating functional groups were easily converted to the desired products through the formation of aluminum hydride as an active species. A kinetic study of the catalytic reaction is also reported.