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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.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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...

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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...

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Hydrogenation Reactions with Heterobimetallic Complexes.

Preshit C Abhyankar¹, Christine M Thomas¹

¹Department of Chemistry and Biochemistry, The Ohio State University, 100 W. 18th Ave. 3109 Newman and Wolfrom, Columbus, Ohio, 43210, United States.

Angewandte Chemie (International Ed. in English)

|October 4, 2024

Summary

Heterobimetallic catalysts, utilizing cooperative metal effects, offer enhanced selectivity and novel pathways for hydrogenation reactions. This review highlights their development for unsaturated substrates.

Keywords:

catalysis heterobimetallic hydrogenation metal-metal cooperativity

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

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Published on: July 30, 2017

Area of Science:

Catalysis and Materials Science
Organic Synthesis

Background:

Hydrogenation reactions are crucial for synthesizing valuable products from basic chemicals.
Multimetallic active sites, particularly heterobimetallic complexes, enhance small molecule activation and catalytic efficiency.
These complexes offer advantages over homo-bimetallic and mono-metallic catalysts in terms of reaction pathways and selectivity.

Purpose of the Study:

To provide a historical overview of heterobimetallic catalyst development for hydrogenation.
To review recent advancements in heterobimetallic catalysis for unsaturated substrates.

Main Methods:

Literature review of heterobimetallic complexes in hydrogenation.
Analysis of cooperative effects in multimetallic active sites.

Main Results:

Heterobimetallic catalysts demonstrate unique reactivity and selectivity in hydrogenation.
Recent research shows significant progress in designing and applying these catalysts.

Conclusions:

Heterobimetallic catalysts represent a promising area for efficient and selective hydrogenation.
Continued development is expected to yield further innovations in catalytic processes.