B -N/ B -H Transborylation: borane-catalysed nitrile hydroboration.

Authors :: Meger F
Kwok ACW
Gilch F
Willcox DR
Hendy AJ
Nicholson K
Bage AD
Langer T
Hunt TA
Thomas SP
Source :: Beilstein journal of organic chemistry [Beilstein J Org Chem] 2022 Sep 26; Vol. 18, pp. 1332-1337. Date of Electronic Publication: 2022 Sep 26 (Print Publication: 2022).
Publication Year :: 2022
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.<br /> (Copyright © 2022, Meger et al.)