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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...
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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...
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Regioselectivity and Stereochemistry of Hydroboration02:36

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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...
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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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.
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Updated: Sep 13, 2025

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
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Reverse electron transfer in Ru/HfB2 drives selective hydrogenation via strong metal-support coupling.

Xianlang Chen1, Chengkang Zhou1, Guoquan Zhou2

  • 1Engineering Research Center of Recycling & Comprehensive Utilization of Pharmaceutical and Chemical Waste of Zhejiang Province, Taizhou University, Taizhou 318000, Zhejiang, China. lrr@tzc.edu.cn.

Chemical Communications (Cambridge, England)
|August 1, 2025
PubMed
Summary

Ruthenium on Hafnium Diboride (Ru/HfB2) catalysts overcome the benzoic acid hydrogenation activity-selectivity trade-off. This breakthrough enables high conversion and selectivity through strong metal-support interactions generating electron-rich ruthenium sites.

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Area of Science:

  • Catalysis
  • Materials Science
  • Chemical Engineering

Background:

  • Benzoic acid hydrogenation is crucial for producing valuable chemicals.
  • A persistent challenge in this reaction is the trade-off between catalyst activity and selectivity.
  • Existing catalysts often struggle to achieve both high conversion rates and desired product selectivity.

Purpose of the Study:

  • To develop a novel catalytic system that overcomes the activity-selectivity trade-off in benzoic acid hydrogenation.
  • To investigate the role of metal-support interactions in enhancing catalytic performance.
  • To achieve high conversion and selectivity for benzoic acid hydrogenation.

Main Methods:

  • Synthesis of Ruthenium supported on Hafnium Diboride (Ru/HfB2) catalyst.
  • Characterization of the catalyst's electronic properties and metal-support interactions using techniques like XPS and TEM.
  • Testing the catalyst's performance in benzoic acid hydrogenation under various conditions.
  • Optimization of reaction parameters to maximize conversion and selectivity.

Main Results:

  • The Ru/HfB2 catalyst demonstrated exceptional performance, exceeding 99% conversion of benzoic acid.
  • High selectivity for the desired hydrogenation products was achieved, surpassing 99%.
  • Strong metal-support interactions were confirmed, leading to the formation of electron-rich ruthenium sites (Ruδ-).

Conclusions:

  • The Ru/HfB2 catalyst effectively resolves the activity-selectivity dilemma in benzoic acid hydrogenation.
  • The strong metal-support interactions are key to generating active and selective ruthenium sites.
  • This catalytic system offers a promising pathway for efficient and selective production of chemicals from benzoic acid.