Al-NiCl(2°)6H2O-THF: A new, mild and neutral system for selective reduction of organic functional groups

Article abstract of DOI:10.1016/S0040-4020(01)82402-9

A mild and neutral reducing system consisting of Al-NiCl(2°)6H₂O-THF has been developed and reacted with a series of organic compounds containing different functional groups in order to evaluate its synthetic utility. It was observed that this system very efficiently reduces the α-enones to the saturated ketones, aromatic aldehydes and ketones to the corresponding alcohols, nitriles and nitroarenes to amines, acid anhydrides and acid chlorides to aldehydes, disulphides to thiols and epoxides to the corresponding alcohols. On the other hand isolated double bonds, carboxylic acids, esters, lactones, primary, benzyl and allyl halides, aliphatic aldehydes and ketones and aliphatic nitro compounds were found to remain inert to this system. Furthermore, the reducing properties of Al-NiCl(2°)6H₂O in several other organic solvents were also studied.