Catalytic Hydroboration of Organic Nitriles Promoted by Aluminum Complex

Article abstract of DOI:10.1002/adsc.201801252

We demonstrate an efficient protocol for the chemoselective hydroboration of organic nitriles with pinacolborane (HBpin) and catecholborane (HBcat) using aluminum alkyl complex [κ²-{2-F?C₆H₄NP(Se)Ph₂}₂Al?(Me)] as a pre-catalyst to afford diboryl amines under solvent-free and mild conditions (60 °C) in high yield. The aluminum complex was prepared by the reaction of [2-F?C₆H₄NHP(Se)Ph₂] 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. (Figure presented.).