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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

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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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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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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.
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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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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

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Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Alkene Metalates as Hydrogenation Catalysts.

Philipp Büschelberger1, Dominik Gärtner2, Efrain Reyes-Rodriguez2

  • 1Institute of Inorganic Chemistry, University of Regensburg, Universitätsstr. 31, 93040, Regensburg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 28, 2016
PubMed
Summary

First-row transition metal complexes, specifically cobaltates and ferrates, show promise as catalysts for hydrogenation reactions. These complexes efficiently catalyze alkene and alkyne hydrogenations under mild conditions, extending to polar substrates like ketones and imines.

Keywords:
cobalthydrogenationironreaction mechanismstransition metals

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Reductive Reactions

Background:

  • First-row transition-metal complexes are crucial for catalytic hydrogenations.
  • Arene/alkene metalates(1-) (M=Co, Fe) represent a distinct class of catalysts with demonstrated activity.
  • Previous research highlights the potential of these complexes in various reductive processes.

Purpose of the Study:

  • To report the synthesis of novel heteroleptic cobaltates and a homoleptic cobaltate complex.
  • To evaluate the catalytic activity of these synthesized complexes in alkene and alkyne hydrogenations.
  • To investigate the catalytic mechanism and substrate scope of these precatalysts.

Main Methods:

  • Synthesis and full characterization of monoanionic cobalt and iron complexes.
  • Evaluation of precatalyst activity in hydrogenation reactions under mild conditions (2 bar H2, room temperature, THF).
  • Mechanistic studies using NMR spectroscopy, ESI mass spectrometry, and poisoning experiments.

Main Results:

  • Successful synthesis of heteroleptic cobaltates [K([18]crown-6)][Co(η4-cod)(η2-styrene)2] and [K([18]crown-6)][Co(η4-dct)(η4-cod)], and homoleptic cobaltate [K(thf)2][Co(η4-dct)2].
  • The synthesized complexes demonstrated competence as precatalysts in alkene hydrogenations.
  • Mechanistic studies revealed a homogeneous catalytic pathway involving redox-neutral π-ligand exchange and H2 activation.
  • The catalytic scope was extended to polar substrates, including ketones and imines.

Conclusions:

  • The synthesized first-row transition-metal complexes are effective precatalysts for hydrogenation reactions.
  • A homogeneous mechanism initiated by ligand exchange and H2 activation governs the catalytic process.
  • These catalysts show potential for a broader range of reductive transformations, including those involving polar substrates.