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Videos de Conceptos Relacionados

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

Eficientes reacciones de acoplamiento cruzado catalizadas por cromo (II) entre los centros de Csp2.

Andreas K Steib1, Olesya M Kuzmina, Sarah Fernandez

  • 1Department of Chemistry, Ludwig-Maximilians-Universität , Butenandtstrasse 5-13, 81377 Munich, Germany.

Journal of the American Chemical Society
|September 24, 2013
PubMed
Resumen

El cloruro de cromo (II) de baja toxicidad cataliza eficientemente las reacciones de acoplamiento cruzado a temperatura ambiente. Este método ofrece una alternativa más ecológica con productos secundarios significativamente reducidos en comparación con otros catalizadores metálicos.

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química organometálica Química orgánica de los metales.
  • La catálisis es la catálisis.

Sus antecedentes:

  • Las reacciones de acoplamiento cruzado son vitales para la formación de enlaces carbono-carbono en la síntesis orgánica.
  • El acoplamiento cruzado tradicional a menudo emplea metales tóxicos o caros, con reacciones secundarias que afectan el rendimiento.
  • El desarrollo de catalizadores eficientes y selectivos sigue siendo un desafío clave en la química sintética.

Objetivo del estudio:

  • Para investigar la actividad catalítica del cloruro de cromo de baja toxicidad en reacciones de acoplamiento cruzado.
  • Para explorar el alcance de este sistema catalítico con varios sustratos orgánicos.
  • Para comparar la eficiencia y la selectividad del acoplamiento catalizado por cromo con otros metales de transición.

Principales métodos:

  • Utilizando el cloruro de cromo (II) como catalizador para reacciones de acoplamiento cruzado.
  • Empleando reactivos de (hetero) arilmagnesio con haluros N-heterocíclicos, cetonas/iminas aromáticas halogenadas y yoduros de alquenilo.
  • Realizar reacciones a 25 °C y analizar el rendimiento del producto y la formación de productos secundarios.

Principales resultados:

  • El cloruro de cromo ((II) cloruro catalizó efectivamente las reacciones de acoplamiento en cuestión de minutos a temperatura ambiente.
  • El catalizador demostró un amplio alcance de sustrato, acoplando diversos reactivos de (hetero) arilmagnesio con varios electrófilos.
  • Se observaron cantidades significativamente más bajas de productos secundarios de homoacoplamiento en comparación con los catalizadores de hierro, cobalto o manganeso.

Conclusiones:

  • El cloruro de cromo (II) de baja toxicidad es un catalizador altamente efectivo para varias reacciones de acoplamiento cruzado.
  • Este método proporciona una alternativa más selectiva y potencialmente más ecológica a los acoplamientos catalizados con metales de transición existentes.
  • El homoacoplamiento reducido ofrece una mayor eficiencia sintética y economía atómica.