Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 18, Issue -, Pages 1332-1337Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.18.138
Keywords
boron; catalysis; hydroboration; nitrile; transborylation
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In this study, a borane-catalysed hydroboration of nitriles to give primary amines is reported, with good yields and chemoselectivity observed. DFT calculations and mechanistic studies support the proposal of a double B-N/B-H transborylation mechanism.
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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