Other than the carbonyl groups, lithium triethylborohydride can reduce primary bromides and tosylates to the corresponding hydrocarbons (Scheme 9). The epoxides are also cleaved to give the alcohols and the hydride is transferred to the less hindered side if epoxides.  Lithium triethylborohydride is called super hydride and an extremely powerful source of hydride.

Scheme 9

M. Zaidlewicz, H. C. Brown, Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons, Inc., L. A. Pauette, Ed., New York, 1995, 5, 3180.

Examples:

N. Toyooka, M. Okumura, H. Nemoto, J. Org. Chem. 2002, 67, 6078.

N. Toyooka, A. Fukutome, H. Nemoto, J. W. Daly, T. F. Spande, H. M. Garraffo, T. Kaneko, Org. Lett. 2002, 4, 1715.

N. Pourahmady, E. J. Eisenbraun, J. Org. Chem. 1983, 48, 3067.

2.1.5.5 Sodium Cyanoborohydride (NaBH₃CN)

NaBH₃CN is less reactive reducing agent than sodium borohydride due to the presence of electron withdrawing cyano group. Reaction of NaBH₄ with HCN gives NaBH₃CN, which is soluble in THF, MeOH, H₂O, HMPA and DMF. NaBH₃CN cannot reduce the aldehydes or ketones in neutral condition but it reduces the protonated aldehydes and ketones at around pH 3 (Scheme 10). The iminium ion could be reduced to the corresponding amine with almost quantitative yield (Scheme 11).

Scheme 10