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

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 chemosel...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2022, Vol.18 (1), p.1332-1337
Main Authors: Meger, Filip, Kwok, Alexander C W, Gilch, Franziska, Willcox, Dominic R, Hendy, Alex J, Nicholson, Kieran, Bage, Andrew D, Langer, Thomas, Hunt, Thomas A, Thomas, Stephen P
Format: Article
Language:English
Subjects:
Amines
Boron
Catalysis
hydroboration
Hydrogenation
nitrile
Reagents
Temperature
transborylation
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Summary: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.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.18.138