The reductive deaminative conversion of nitriles to alcohols using para-formaldehyde in aqueous solution

Abstract

We report herein, for the first time, the application of para-formaldehyde (pFA) to the reductive deamination of both aliphatic and aromatic nitriles in aqueous solution under transfer hydrogenation conditions. A broad range of primary alcohols have been synthesized selectively with very good to excellent yields under the optimized conditions. The study disclosed that the air-stable, inexpensive and commercially available catalyst [Ru(p-cymene)Cl₂]₂ acts as the catalyst precursor in this reaction, converting to other more active catalytic species in the presence of pFA, resulting in its degradation to CO₂ and H₂. Nitriles are also showed to play a dual role in this transformation, both as a substrate and as a ligand, where the dimeric catalyst structures convert to monomeric ones upon the coordination of nitrile molecules.