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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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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Hydroboration-Oxidation of Alkenes03:08

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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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...
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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.
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 reactions,...
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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 stereochemistry.
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Metallic Barium: A Versatile and Efficient Hydrogenation Catalyst.

Philipp Stegner1, Christian Färber1, Ulrich Zenneck1

  • 1Chair of Inorganic and Organometallic Chemistry, Universität Erlangen-Nürnberg, Egerlandstrasse 1, 91058, Erlangen, Germany.

Angewandte Chemie (International Ed. in English)
|November 12, 2020
PubMed
Summary

Activated barium (Ba) metal serves as a potent hydrogenation catalyst, outperforming existing group 2 metal catalysts. It efficiently reduces diverse organic compounds, including alkenes, aromatic hydrocarbons, and nitrogen-containing heterocycles, via proposed metal hydride and Ba metal cycles.

Keywords:
alkaline earth metalsbariumhydridehydrogenation catalysismetal activation

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Area of Science:

  • Heterogeneous Catalysis
  • Organometallic Chemistry
  • Materials Science

Background:

  • Development of efficient hydrogenation catalysts is crucial for organic synthesis.
  • Group 2 metal catalysts have shown promise but require further enhancement.
  • Barium (Ba) metal's catalytic potential in hydrogenation remains largely unexplored.

Purpose of the Study:

  • To synthesize and characterize activated barium (Ba) metal as a hydrogenation catalyst.
  • To evaluate the catalytic activity of Ba metal for a wide range of organic substrates.
  • To elucidate the catalytic mechanisms involved in Ba-mediated hydrogenation.

Main Methods:

  • Barium (Ba) metal activation via evaporation and co-condensation with heptane.
  • Hydrogenation reactions using activated Ba metal powder with various organic substrates.
  • Density Functional Theory (DFT) calculations to model catalytic pathways.

Main Results:

  • Activated Ba metal powder exhibits high catalytic activity for hydrogenation.
  • Ba metal outperforms previously known group 2 metal catalysts in hydrogenation.
  • Proposed catalytic cycles include a classical metal hydride pathway and a Ba metal cycle.

Conclusions:

  • Activated Ba metal is a highly effective and versatile hydrogenation catalyst.
  • The catalytic performance of Ba metal surpasses existing group 2 metal catalysts.
  • DFT calculations support the proposed mechanisms, highlighting Ba's accelerating role.