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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Reacciones de cicloadición dearomativas de trimetilenometano y cicloadición catalizadas por el paladio.

Barry M Trost1, Veronika Ehmke, B Michael O'Keefe

  • 1Department of Chemistry, Stanford University , Stanford, California 94305, United States.

Journal of the American Chemical Society
|May 31, 2014
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Este estudio introduce una nueva reacción catalizada por paladio para la dearomatización de nitroarenos en compuestos alicíclicos. El método es versátil e incluye una variante enantioselectiva para la síntesis asimétrica.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • La catálisis es la catálisis.
  • Metodología sintética de la metodología sintética.

Sus antecedentes:

  • Los nitroarenos son bloques de construcción sintéticos comunes.
  • Las reacciones de dearomatización ofrecen nuevas vías a complejas estructuras cíclicas.
  • La dearomatización asimétrica es una transformación desafiante pero valiosa.

Objetivo del estudio:

  • Desarrollar un protocolo general para el trimetilenometano dearomativo [3+2] cícloadición catalizado por paladio con nitroarenos.
  • Para lograr la formación exclusiva de productos alicíclicos aromatizados.
  • Para establecer una variante enantioselectiva de este querido proceso de romatización.

Principales métodos:

  • Reacción de cicloadición [3+2] catalizada por el paladio.
  • Utilizando sustratos de nitroareno.
  • Empleando ligandos quirales de bisdiamidofosfito para la enantioselectividad.

Principales resultados:

  • Se estableció un protocolo general para la desaromatización de los nitroarenos.
  • Se logró la formación exclusiva de productos alicíclicos dearomatizados.
  • Se desarrolló una variante enantioselectiva utilizando ligandos quirales, lo que demuestra la catálisis asimétrica.

Conclusiones:

  • La metodología descrita proporciona una ruta robusta a los compuestos alicíclicos desaromatizados de los nitroarenos.
  • La reacción exhibe un amplio alcance de sustrato, incluyendo los sistemas heterocíclicos y bencenoides.
  • El desarrollo de una variante enantioselectiva pone de relieve un raro ejemplo de dearomatización catalítica asimétrica.