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

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

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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.
Original languageEnglish
Pages (from-to)1332-1337
JournalBeilstein Journal of Organic Chemistry
Volume18
Early online date26 Sept 2022
DOIs
Publication statusE-pub ahead of print - 26 Sept 2022

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