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

Autor: Filip Meger, Alexander C. W. Kwok, Franziska Gilch, Dominic R. Willcox, Alex J. Hendy, Kieran Nicholson, Andrew D. Bage, Thomas Langer, Thomas A. Hunt, Stephen P. Thomas
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 18, Iss 1, Pp 1332-1337 (2022)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.18.138
Popis: 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.
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