Related Experiment Video
Updated: Jun 3, 2026
08:40
Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
Published on: December 6, 2021
Nickel nanoparticles in hydrogen transfer reactions
Francisco Alonso1, Paola Riente, Miguel Yus
1Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Síntesis Orgánica, Universidad de Alicante, Spain. falonso@ua.es
Accounts of Chemical Research
|March 23, 2011
Summary
This study introduces nickel nanoparticles as a cost-effective alternative to noble metals for transfer hydrogenation and hydrogen autotransfer reactions. These nickel catalysts efficiently facilitate various organic transformations, including olefin reduction and alcohol activation, offering a greener approach to synthesis.
Area of Science:
- Green Chemistry and Sustainable Catalysis
- Nanoparticle Catalysis
- Organic Synthesis
Background:
- Transfer hydrogenation and hydrogen autotransfer reactions are safer, more environmentally friendly alternatives to traditional reduction methods.
- Noble metal catalysts (Ru, Pd) dominate these transformations, but their high cost limits broader application.
- Research into cheaper, catalytically active metals for these reactions has been comparatively neglected.
Purpose of the Study:
- To develop and demonstrate the efficacy of nickel(0) nanoparticles as a substitute for expensive noble metal catalysts.
- To explore the application of nickel nanoparticles in both transfer hydrogenation and hydrogen autotransfer reactions.
- To investigate the catalytic activity of nickel nanoparticles in key organic transformations, including alkylation and olefination.
Main Methods:
- Synthesis and characterization of nickel(0) nanoparticles.
- Catalytic testing of nickel nanoparticles in transfer hydrogenation of olefins and carbonyl compounds using 2-propanol as the hydrogen donor.
- Application of nickel nanoparticles in hydrogen autotransfer reactions, including α-alkylation of ketones, reductive aza-Wittig reactions, and Wittig-type olefination.
Main Results:
- Nickel nanoparticles effectively catalyzed transfer hydrogenation and reductive amination without requiring a base, with easy catalyst reuse.
- Nickel nanoparticles enabled the activation of primary alcohols for α-alkylation of ketones and reductive aza-Wittig synthesis of secondary amines, replacing noble metals.
- Nickel nanoparticles facilitated a one-pot synthesis of stilbenes from alcohols via Wittig-type olefination, including the natural product resveratrol.
Conclusions:
- Nickel(0) nanoparticles represent a highly effective and economical alternative to noble metals for a range of important organic transformations.
- The demonstrated catalytic activity and reusability of nickel nanoparticles highlight their potential for sustainable and cost-efficient chemical synthesis.
- This work expands the scope of non-noble metal catalysis in transfer hydrogenation and hydrogen autotransfer methodologies.
Related Concept Videos
02:50Catalysis
The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
02:13Reduction of Alkenes: Catalytic Hydrogenation
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
01:20Electrophilic Aromatic Substitution: Nitration of Benzene
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
01:03Precipitation Gravimetry
Precipitation gravimetry is based on converting an analyte into a sparingly soluble precipitate, which is separated by filtration and weighed. An ideal precipitate should be pure, insoluble, of known composition, and easily filtered from the reaction mixture.
In determining nickel by gravimetric analysis, a precipitant of ethanolic dimethylglyoxime is added to a hot nickel salt solution. This is quickly followed by the dropwise addition of dilute ammonia solution until precipitation occurs. A...
In determining nickel by gravimetric analysis, a precipitant of ethanolic dimethylglyoxime is added to a hot nickel salt solution. This is quickly followed by the dropwise addition of dilute ammonia solution until precipitation occurs. A...