Reduction of nitriles with aminoborane under mild reaction conditions

ORGN 635

Lubov Pasumansky and Bakthan Singaram, singaram@chemistry.ucsc.edu. Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High St., Santa Cruz, CA 95064
Monomeric diisopropylaminoborane (H2BN(iPr)2) promotes the reduction of a variety of nitriles to their corresponding primary amines in good yields and purity.  Diisopropylaminoborane was generated in situ from lithium diisopropylaminoborohydride (LiH3BN(iPr)2) and methyl iodide.  It should be pointed out that lithium diisopropylaminoborohydride itself does not reduce nitriles at room temperature.