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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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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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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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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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Alcohols from Carbonyl Compounds: Reduction02:23

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.                                       ...
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Descarbonización reductora catalizada por el níquel de los alquenos

Andrés García-Domínguez1, Zhaodong Li1, Cristina Nevado1

  • 1Department of Chemistry, University of Zurich , Winterthurerstrasse 190, Zurich CH 8057, Switzerland.

Journal of the American Chemical Society
|May 11, 2017
PubMed
Resumen

Este estudio introduce una nueva reacción de tres componentes para la dicarbofuncionalización del alqueno. La catálisis de níquel y el reductor TDAE crean eficientemente nuevos enlaces carbono-carbono en condiciones suaves.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • La funcionalización de alceno es crucial en la síntesis orgánica.
  • El desarrollo de métodos eficientes para la formación de enlaces C-C sigue siendo un desafío clave.

Objetivo del estudio:

  • Para presentar una nueva dicarbofuncionalización reductiva intermolecular de tres componentes de los alquenos.
  • Establecer un método para la formación de enlaces Csp3-Csp3 y Csp3-Csp2.

Principales métodos:

  • Utilizando la catálisis del níquel (Ni).
  • Utilizando Tetrakis (dimetilamino) etileno (TDAE) como el reductor terminal.
  • Activación secuencial de dos electrófilos diferentes.

Principales resultados:

  • Dicarbofuncionalización exitosa de varios sistemas π.
  • Formación directa de enlaces Csp3-Csp3 y Csp3-Csp2.
  • Se observa una selectividad exquisita en condiciones de reacción suaves.

Conclusiones:

  • El método desarrollado ofrece una vía versátil para la funcionalización de alceno.
  • El sistema Ni/TDAE proporciona un enfoque catalítico eficiente.
  • Este trabajo amplía el conjunto de herramientas para la construcción de moléculas orgánicas complejas.