<i>B</i>–N/<i>B</i>–H Transborylation: borane-catalysed nitrile hydroboration

Abstract

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 <i>B</i>-N/<i>B</i>-H transborylation mechanism.