The NiCl2·2H2O-Li-arene combination as reducing system. Part 3. Reduction of carbonyl compounds and imines

Article abstract of DOI:10.1016/S0040-4020(97)10406-9

The reaction of different carbonyl compounds or their imines with a mixture of nickel(II) chloride dihydrate, an excess of lithium powder and a catalytic amount of naphthalene (16 mol %) or DTBB (8 mol %) in THF at room temperature, leads to the formation of the corresponding alcohols or amines, respectively. The incorporation of deuterium oxide into the nickel salt complex yields the corresponding deuterated products. The process can also be applied to α,β-unsaturated carbonyl compounds leading either to the hydrogenation of only the carbon-carbon double bond or the full hydrogenation, depending on the amount of the nickel salt and/or reaction times.