B – N/B – 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 B–N/B–H transborylation mechanism.

Beilstein J. Org. Chem. 2022, 18, 1332–1337. doi:10.3762/bjoc.18.138

Source: Beilstein Journal of Organic Chemistry - September 26, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: boron catalysis hydroboration nitrile transborylation Letter Source Type: research