Categories: N-H Bond Formation >
Reduction of nitriles
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Recent Literature
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.
D. Haddenham, L. Pasumansky, J. DeSoto, S. Eagon, B. Singaram, J. Org. Chem., 2009,
74, 1964-1970.
Odorless Dod-S-Me and MMS are developed as efficient borane carriers. The
yields of hydroborations and reductions with the borane complex of Dod-S-Me
are very high. The recovery of Dod-S-Me after the reaction is quantitative.
P. K. Patra, K. Nishide, K. Fuji, M. Node, Synthesis, 2004,
1003-1006.
The scope of nickel boride mediated reduction of nitriles has been extended
further to allow the preparation of Boc protected amines via a mild
catalytic process.
S. Caddick, D. B. Judd, A. K. de K. Lewis, M. T. Reich, M. R. V. Williams,
Tetrahedron, 2003, 59, 5417-5423.
