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Videos de Conceptos Relacionados

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.5K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
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...
3.8K
Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.2K
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.
2.2K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.5K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.5K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.1K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Acoplamiento reductivo de relevos radicales asimétricos catalizados por Ni

Xiaofeng Wei1, Wei Shu1, Andrés García-Domínguez1

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

Journal of the American Chemical Society
|June 30, 2020
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce una nueva dicarbofuncionalización reductora asimétrica catalizada por níquel de los alquenos. Este método crea eficientemente estructuras alifáticas quirales utilizando haluros y olefinas fácilmente disponibles con alta estereoselectividad.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis asimétrica

Sus antecedentes:

  • La dicarbofuncionalización de alceno es crucial para la síntesis de compuestos alifáticos.
  • Las variantes asimétricas catalíticas para esta transformación son limitadas.
  • Las estrategias de acoplamiento reductivo ofrecen ventajas potenciales.

Objetivo del estudio:

  • Desarrollar una dicarbofuncionalización reductora catalizada por níquel intermolecular altamente eficiente de los alquenos.
  • Para permitir la adición simultánea de haluros Csp2 y Csp3 a través de varias olefinas.
  • Lograr una alta regioselectividad y enantioselectividad en la síntesis de bloques quirales.

Principales métodos:

  • Utilizó un enfoque de reducción de la dicarbofuncionalidad catalizada por níquel.
  • Se utilizan haluros Csp2 y Csp3 fácilmente disponibles como electrófilos.
  • Investigó la reacción con amidas de vinilo, boranos de vinilo y fosfonatos de vinilo a temperatura ambiente.
  • Aprovecho un intermediario quiral de alquilo Ni (III) generado in situ para el control estéreo.

Principales resultados:

  • Se ha logrado una dicarbofuncionalización altamente regioselectiva y enantioselectiva de los alquenos.
  • Demostró la adición simultánea de dos electrófilos distintos a través de las olefinas.
  • Se ha empleado con éxito un ligando quiral de bisoxazolina (l) - ((+)) -isoleucina para la formación de enlaces Csp3-Csp2 estereodefinidos.
  • Se demostró la síntesis de amidas quirales a través de acoplamientos reductores retransmitidos por radicales asimétricos (ARRRC).

Conclusiones:

  • Presentó una nueva y eficiente dicarbofuncionalización reductora catalizada por níquel intermolecular de alquenos.
  • Destacó la utilidad sintética de la metodología para ensamblar bloques de construcción quirales como aminas y oxazolinas.
  • Se estableció una nueva vía para la formación de enlaces Csp3-Csp2 estereocontrolados sin reactivos organometálicos sensibles.