Science of Synthesis

Chciuk, T. V.; Flowers, R. A., II, Science of Synthesis Knowledge Updates, (2016) 2, 230.

The formation of aliphatic amines is often accomplished through the use of harsh reagents such as lithium aluminum hydride. Instantaneous reduction of the nitro group, even in the presence of other functional groups, can be accomplished using samarium(II) iodide in the presence of water and an amine, to generate the corresponding amines in good yields (‌Scheme 60‌).[‌94‌] Unfortunately, for substrates with α,β-unsaturation adjacent to the nitro group the yields drop significantly, which is likely due to competing reduction of the conjugated alkene.

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