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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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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 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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Radical Oxidation of Allylic and Benzylic Alcohols01:21

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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
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Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

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Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Hidrogenaciones catalíticas selectivas de nitriles, cetonas y aldehídos por complejos de pinzas de manganeso bien

Saravanakumar Elangovan1, Christoph Topf1, Steffen Fischer2

  • 1Leibniz-Institut für Katalyse e.V. , Albert Einstein Straße 29a, 18059 Rostock, Germany.

Journal of the American Chemical Society
|May 25, 2016
PubMed
Resumen

Los nuevos catalizadores de manganeso permiten la hidrogenación selectiva de grupos funcionales polares utilizando hidrógeno molecular. Esto ofrece una ruta de síntesis más ecológica para aminas y alcoholes valiosos, beneficiando a industrias como el sabor y la fragancia.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química ecológica

Sus antecedentes:

  • Las hidrogenaciones son clave para las transformaciones limpias de grupos funcionales.
  • La reducción selectiva de nitriles, cetonas y aldehídos produce aminas y alcoholes.
  • El desarrollo de catalizadores busca sistemas eficientes y ampliamente aplicables, con un enfoque reciente en los metales abundantes en la Tierra.

Objetivo del estudio:

  • Introducir nuevos complejos de manganeso definidos molecularmente para la hidrogenación.
  • Demostrar la actividad catalítica de estos complejos de manganeso en grupos funcionales polares.

Principales métodos:

  • Síntesis de complejos específicos de manganeso definidos molecularmente.
  • Aplicación de estos complejos como catalizadores para reacciones de hidrogenación.
  • Optimización de las condiciones de reacción para la tolerancia del grupo funcional.

Principales resultados:

  • Primer informe de complejos de manganeso definidos molecularmente que catalizan la hidrogenación.
  • Hidrogenación exitosa de varios grupos funcionales polares.
  • Reducción selectiva de sustratos industrialmente relevantes, incluidos los de la industria de sabores y fragancias.

Conclusiones:

  • Los complejos de manganeso ofrecen una alternativa prometedora para la hidrogenación catalítica.
  • Los catalizadores desarrollados muestran una buena tolerancia y selectividad del grupo funcional.
  • Este trabajo contribuye al desarrollo de procesos catalíticos sostenibles utilizando metales abundantes en la Tierra.