9-Borabicyclo[3.3.1]nonane is a mild reagent for the reduction of carbonyl compounds, acid chlorides and alkenes. As 9-BBN does not form complexes with tertiary amines, a stoichiometric amount of the reagent is sufficient for the complete reduction of amides to amines.
The combination of B2pin2 and KOtBu enables a chemoselective, metal-free reduction of aromatic nitro compounds to the corresponding amines in very good yields in isopropanol. The reaction tolerates various reducible functional groups.
H. Lu, Z. Geng, J. Li, D. Zou, Y. Wu, Y. Wu, Org. Lett., 2016, 18, 2774-2776.