Efficient Selective Reduction of Aromatic Nitro Compounds Affording Aromatic Amines under CO/H2O Conditions Catalyzed by Amine-Added Rhodium-Carbonyl Complexes.

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Remarkably high catalytic activities for the reduction of aromatic nitro compounds affording aromatic amines using CO (1 atm) and water at room temperature were exhibited by using amine-added rhodium carbonyl complexes (Rh(CO)2(acac), Rh4(CO)12, and Rh6(CO)16) in 2-methoxyethanol or diglyme (diethylene glycol dimethyl ether) containing a 5 equiv NaOH aqueous solution. The reduction proceeded not only with high catalytic activities, but also with remarkably high nitro-group selectivities, as exhibited in the case of 1-nitroanthraquinone affording 1-aminoanthraquinone, without any other unsaturated groups, such as C=O, being reduced. The T. O. F. (turnovers/time) of 1776 mol-cat−1 h−1 (296 g-atom Rh−1 h−1) was attained for the reduction of p-nitroanisole yielding p-anisidine using Rh6(CO)16-1,8-bis(dimethylamino)-naphthalene catalyst.
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