B -N/ B -H Transborylation: borane-catalysed nitrile hydroboration.
Filip S MegerAlexander C W KwokFranziska GilchDominic R WillcoxAlex J HendyKieran NicholsonAndrew D BageThomas LangerThomas A HuntStephen P ThomasPublished in: Beilstein journal of organic chemistry (2022)
The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48-95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a double B -N/ B -H transborylation mechanism.