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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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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 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.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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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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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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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Highly active cationic cobalt(II) hydroformylation catalysts.

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New cationic cobalt catalysts offer high activity and selectivity for alkene hydroformylation, approaching rhodium performance. These catalysts demonstrate long lifetimes and stability, particularly for internal alkenes.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Hydroformylation traditionally uses cobalt or rhodium catalysts.
  • Rhodium catalysts are highly active but expensive.
  • Existing cobalt catalysts have limitations in activity and selectivity.

Purpose of the Study:

  • To develop novel cobalt catalysts with enhanced activity and selectivity.
  • To compare the performance of new cobalt catalysts with existing industrial standards.
  • To investigate the regioselectivity of these catalysts for different alkene types.

Main Methods:

  • Synthesis of cationic cobalt(II) bisphosphine hydrido-carbonyl complexes.
  • Evaluation of catalytic activity in alkene hydroformylation.
  • Analysis of linear-to-branched (L:B) regioselectivity for various alkenes.
  • Assessment of catalyst stability and lifetime.

Main Results:

  • New cationic cobalt catalysts exhibit significantly higher activity than traditional cobalt(I) catalysts.
  • Catalyst activity approaches that of expensive rhodium-phosphine catalysts.
  • Low L:B regioselectivity observed for simple linear alkenes.
  • High L:B regioselectivity achieved for internal alkenes with alkyl branches due to isomerization and steric effects.
  • Catalysts demonstrate long lifetimes and resistance to degradation.

Conclusions:

  • Cationic cobalt bisphosphine catalysts represent a promising advancement in hydroformylation.
  • These catalysts offer a cost-effective alternative to rhodium catalysts.
  • Tailored selectivity for internal alkenes is achievable with these new systems.