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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction 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...

Reduction of Alkenes: Catalytic Hydrogenation

Reduction 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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction 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.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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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...

Catalysis

Catalysis

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.

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...

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A Selective Iron(I) Hydrogenation Catalyst.

Niko Sila¹, Andreas Dürrmann², Birgit Weber²

¹Inorganic Chemistry II-Catalyst Design, Sustainable Chemistry Center, University of Bayreuth, 95440 Bayreuth, Germany.

Journal of the American Chemical Society

|September 23, 2024

Summary

This summary is machine-generated.

This study introduces a novel iron(I) catalyst for hydrogenation reactions. It activates hydrogen and efficiently hydrogenates polar double bonds, showcasing broad functional group tolerance.

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Published on: December 6, 2021

Area of Science:

Organometallic Chemistry
Catalysis
Sustainable Chemistry

Background:

Iron is an abundant and cost-effective transition metal with significant potential in catalysis.
Understanding iron's role in chemical transformations is crucial for developing sustainable technologies.
Existing hydrogenation catalysts often face limitations regarding functional group compatibility.

Purpose of the Study:

To report a novel iron(I) complex as an effective hydrogenation catalyst.
To elucidate the catalytic mechanism, focusing on hydrogen activation and substrate hydrogenation.
To demonstrate the catalyst's tolerance towards various functional groups.

Main Methods:

Synthesis and characterization of the iron(I) complex.
Kinetic studies to determine reaction rates and orders.
Mechanistic investigations including isotopic labeling and computational studies.
Testing the catalyst's performance with various substrates containing hydrogenation-sensitive groups.

Main Results:

The iron(I) catalyst activates hydrogen via heterolytic bond cleavage, forming a monohydride intermediate.
Hydrogenation of polar double bonds proceeds through a bimetallic pathway involving potassium-assisted hydride transfer.
The catalytic mechanism avoids oxidative addition and reductive elimination pathways.
The catalyst demonstrates excellent tolerance for hydrogenation-sensitive functional groups, including carbonyls (C═O).

Conclusions:

A novel iron(I) hydrogenation catalyst has been developed.
The elucidated mechanism offers a new perspective on iron-catalyzed hydrogenation.
This catalyst represents a promising advancement for selective hydrogenation in complex molecules.