Alkene Hydrogenations by Soluble Iron Nanocluster Catalysts
Tim N Gieshoff1, Uttam Chakraborty1, Matteo Villa1
1Institute of Organic Chemistry, University of Regensburg, Universitätsstrasse 31, 93040, Regensburg, Germany.
Angewandte Chemie (International Ed. in English)
|February 25, 2017
Summary
This study introduces an iron-catalyzed hydrogenation method for alkenes, offering a sustainable alternative to noble metals. The new protocol shows high activity and broad scope under mild conditions.
Area of Science:
- Sustainable chemistry
- Catalysis
- Organometallic chemistry
Background:
- Noble metal catalysts dominate alkene hydrogenation.
- Developing earth-abundant metal catalysts is crucial for sustainable synthesis.
- Iron catalysis offers a promising avenue for replacing noble metals.
Purpose of the Study:
- To develop an iron-catalyzed hydrogenation protocol for challenging alkene substrates.
- To achieve high catalytic activity and broad substrate scope under mild conditions.
- To investigate the catalytic mechanism involving iron nanoclusters.
Main Methods:
- Iron-catalyzed hydrogenation of tri- and tetra-substituted alkenes.
- Utilizing mild reaction conditions (1-4 bar H2, 20°C).
- Isolation and characterization of novel iron nanocluster architectures.
Main Results:
- An iron-catalyzed hydrogenation protocol with unprecedented activity and scope was established.
- The protocol is effective for tri- and tetra-substituted alkenes under mild conditions.
- Novel iron nanocluster architectures were identified as catalyst reservoirs and seeds for particle growth.
Conclusions:
- Iron catalysis can effectively replace noble metals in alkene hydrogenation.
- The developed protocol offers a sustainable and efficient method for alkene functionalization.
- Understanding iron nanocluster behavior provides insights into homogeneous and heterogeneous catalysis.
More Related Videos
Related Concept Videos
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
4.0K
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...
4.0K
02:13Reduction of Alkenes: Catalytic Hydrogenation
14.6K
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...
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...
14.6K
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
9.2K
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.
9.2K
01:22Heterogeneous Catalysis
41
Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
41
01:28Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
6.2K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
6.2K
02:50Catalysis
31.3K
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.
31.3K