New Method for the Reduction of Benzophenones with Raney Ni‐Al Alloy in Water

Abstract

Raney Ni-Al alloy in a dilute alkaline aqueous solution has been shown to be a powerful reducing agent, which is highly effective in the reduction of benzophenones to the corresponding hydrocarbon derivatives, in the absence of any organic solvents.

A Review on the Recent Advances in the Reductions of Carbon–Carbon/Oxygen Multiple Bonds Including Aromatic Rings Using Raney Ni–Al Alloy or Al Powder in the Presence of Noble Metal Catalysts in Water

“…The chemoselective reduction of various carbonyl compounds to alcohols with ammonia-borane, a non-toxic, environmentally benign and easily handled reagent in neat water was achieved and with quantitative conversion and a high isolated yield [93]. Previously, benzophenone was selected as the model compound for the reduction of the carbonyl group as well as the aromatic rings [94,95]. Yamato et al have also explored the reduction of benzophenone using Raney Ni-Al alloy and Al powder in the presence of a noble metal catalyst in water at a relatively low temperature in a sealed tube [96].…”

“…Thereafter, benzophenones have been easily reduced to the corresponding hydrocarbon derivatives using Raney Ni-Al alloy in a dilute alkaline aqueous solution without the need for any organic solvents [95]. This method was also used for the reduction of alkylbenzils and alkoxybenzils under similar reaction conditions [134].…”

The Dibenzosuberenone Scaffold as a Privileged Substructure: From Synthesis to Application

“…Furthermore, the reduction of 5-dibenzosuberenone (1) to the hydrocarbon 272 in good yield was also realized using Raney Ni-Al alloy in a dilute alkaline solution as a powerful reducing agent (Scheme 44). 174 Hydrocarbons 273-275 are potential intermediates for pharmacologically important compounds (Scheme 45). 175 Dehydration of the C10-C11 deuterated hydroxy ester 275b in acetic acid containing p-toluenesulfonic acid resulted in the incorporation of deuterium at C5 of 273b with a k H /k D of 2.76.…”

Reduction of carbonyl compounds by Raney Ni–Al alloy and Al powder in the presence of noble metal catalysts in water

“…Previously, benzophenone was selected as the model compound for the reduction of the carbonyl group as well as the aromatic rings [21,33]. In our present study, we also explored the reduction of carbonyl group using Raney Ni-Al alloy and aromatic rings of benzophenone with Raney Ni-Al alloy and Al powder in presence of Pt/C in water at a relatively lower temperature in a sealed tube.…”

“…Raney Ni-Al was found to be very efficient in the reduction of phenol, naphthalenes, biphenyls, acenaphthene and dechlorination of mono and dichlorobiphenyls to the corresponding hydrocarbon derivatives, in the absence of organic solvents at 90 8C in dilute aqueous alkaline solution. The reduction of benzophenones was also carried out using Raney Ni-Al in water with KOH and other alkaline earth hydroxides [19][20][21][22]. Xia et.al.…”