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

Rayhan, Ummey; Do, Jung-He; Arimura, Takashi; Yamato, Takehiko

doi:10.1016/j.crci.2014.10.011

Cited by 10 publications

(10 citation statements)

References 34 publications

(31 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These results clearly show that a transition-metal catalyst increases the reducing capability of Raney Ni-Al as also reported previously by our group. 46 Guo-Bin Liu et al reported that Raney Ni-Al alloy in a dilute alkaline aqueous solution becomes a powerful reducing agent, which is highly effective in the reduction of benzophenones to the corresponding hydrocarbon derivatives without using any organic solvent. 35 In our case, reduction of phenylacetylene (1a) to the corresponding hydrocarbon derivatives is achieved in water without using any alkaline solution and under mild reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

“…45 Previously, we reported the reduction of carbonyl compounds by Raney Ni-Al alloy and Al powder in the presence of noble metal catalysts in water. 46 Herein, we illustrate a simple reduction method for the alkyne group as well as an aromatic ring using commercially available Raney Ni-Al alloy and Al powder in the presence of a noble metal catalyst (Pt/C, Pd/C, Ru/C or Rh/C) in water in a sealed tube.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Reduction of phenylacetylenes using Raney Ni–Al alloy, Al powder in the presence of noble metal catalysts in water

Yamato¹,

Rayhan²,

Kowser³

et al. 2017

Arkivoc

Self Cite

View full text Add to dashboard Cite

The chemoselective reduction is based on the reaction between Al either as powder or from the alloy and water which generates in situ hydrogen to effect the reduction of the targeted functional groups. Raney Ni-Al alloy with Al powder can reduce phenylacetylenes to the corresponding ethylbenzene (3) in water in excellent yield at 120 °C for 6 h in a sealed tube. In addition, the complete reduction of the aromatic ring to ethylcyclohexane required 60 o C for 12 h with Raney Ni-Al alloy, Al powder in the presence of Pt/C. Appropriate selection of reaction conditions allowed the selective preparation of ethylbenzene as well as ethylcyclohexane from phenylacetylene.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Reduction of phenylacetylenes using Raney Ni–Al alloy, Al powder in the presence of noble metal catalysts in water

Yamato¹,

Rayhan²,

Kowser³

et al. 2017

Arkivoc

Self Cite

View full text Add to dashboard Cite

show abstract

“…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].…”

Section: A Hydrogenation Of Carbonyl Groupmentioning

confidence: 99%

“…Scheme 3. Reduction of benzophenones using Raney Ni-Al alloy, Al powder and Pt/C in H2O[96].…”

mentioning

confidence: 99%

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

et al. 2018

Self Cite

View full text Add to dashboard Cite

Over the last few years, heterogeneous catalysts have attracted much attention with a view to lowering reaction temperatures and improving the selectivity of many organic syntheses. When designing or optimizing a catalyst, attention is devoted to the nature of the active sites, and how they interact with the reactants, intermediates and products of the catalytic process. It has become clear that the structural and electronic features of an active site are usually affected by the chemical environment in which it operates. Raney Ni-Al alloy and noble metal catalysts such as Ru/C, Rh/C, Pd/C and Pt/C are employed in the selective and complete hydrogenation of various functional groups and aromatic rings in presence of water in a sealed tube. Al powder was found to be capable of reducing a carbonyl group, an alkyne group and the aromatic ring of biphenyl, fluorene, 9,10-dihydroanthracene, polyarenes and N-heterocycles using noble metal catalysts in water under mild reaction conditions.

show abstract

“…Consequently, when using this catalyst, the reaction temperature was gradually decreased and a 91% yield of compound 5a was obtained at 80 °C over 15 h. Thus Pt/C turned out to be the best catalyst and it is well-known that Pt/C can act as a more effective catalyst when used in the presence of Raney Ni-Al alloy and Al powder. 61 The intermediate product diphenylethane was also investigated under the same reaction conditions and it led to excellent yields via the reduction of both aromatic rings. Subsequently, the reduction of substituted diphenylacetylenes was examined to afford compounds 3 and 5.…”

Section: Mmentioning

confidence: 99%

Reduction of diphenylacetylene using Al powder in the presence of noble metal catalysts in water

et al. 2016

Self Cite

View full text Add to dashboard Cite

Diphenylacetylenes can be reduced to the corresponding diphenylethanes (2) in water in excellent yield using Al powder and Pd/C at 60 °C for 3 h in a sealed tube. In addition, the complete reduction of both aromatic rings required 80 °C for 15 h with Al powder in the presence of Pt/C. However, the nature of hydrogenated product formed was found to be strongly influenced by the reaction temperature, time, volume of water and the amount of catalyst being employed.

show abstract

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

Cited by 10 publications

References 34 publications

Reduction of phenylacetylenes using Raney Ni–Al alloy, Al powder in the presence of noble metal catalysts in water

Reduction of phenylacetylenes using Raney Ni–Al alloy, Al powder in the presence of noble metal catalysts in water

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

Reduction of diphenylacetylene using Al powder in the presence of noble metal catalysts in water

Contact Info

Product

Resources

About