A simple
and efficient copper-catalyzed selective transfer hydrogenation
of nitriles to primary amine-boranes and secondary amines with an
oxazaborolidine–BH3 complex is reported. The selectivity
control was achieved under mild conditions by switching the solvent
and the copper catalysts. More than 30 primary amine-boranes and 40
secondary amines were synthesized via this strategy in high selectivity
and yields of up to 95%. The strategy was applied to the synthesis
of 15N labeled in 89% yield.
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