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Reductions of Aliphatic and Aromatic Nitriles to Primary Amines with Diisopropylaminoborane

Dustin Haddenham, Lubov Pasumansky, Jamie DeSoto, Scott Eagon and Bakthan Singaram*

*Department of Chemistry and Biochemistry, University of California, Santa Cruz, 1156 High Street, Santa Cruz, California 95064, Email: singaramchemistry.ucsc.edu

D. Haddenham, L. Pasumansky, J. DeSoto, S. Eagon, B. Singaram, J. Org. Chem., 2009, 74, 1964-1970.

DOI: 10.1021/jo8023329 (free Supporting Information)


Abstract

Diisopropylaminoborane [BH2N(iPr)2] in the presence of a catalytic amount of lithium borohydride (LiBH4) reduces a large variety of aliphatic and aromatic nitriles in excellent yields.BH2N(iPr)2 can also reduce nitriles in the presence of unconjugated alkenes and alkynes. Unfortunately, selective reduction of a nitrile in the presence of an aldehyde is not possible.

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Methods for the preparation of diisopropylaminoborane

Method 1 allows the preparation of pure diisopropylamine, whereas method 2 generates traces of LiBH4. A solution of diisopropylaminoborane prepared with method 2 has been used for the reduction of nitriles.



Key Words

reduction of nitriles, diisopropylaminoborane


ID: J42-Y2009-0790