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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.

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

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

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.

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

Cycloaddition Reactions: Overview

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 Photochemical Activation

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...

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Video Experimental Relacionado

Updated: Oct 16, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Acoplamiento catalizado por hierro de tres reactivos

Guillaume Lefèvre¹

¹Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, CSB2D, 75005 Paris, France.

Science (New York, N.Y.)

|October 21, 2021

Resumen

Los boronatos de vinilo permiten una eficiente formación de enlaces carbono-carbono. Esta reacción de acoplamiento se produce en condiciones suaves, por lo que es una herramienta versátil para la síntesis orgánica.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

La formación de enlaces carbono-carbono es fundamental en la síntesis orgánica.
Los boronatos de vinilo son bloques de construcción versátiles.

Objetivo del estudio:

Desarrollar un método de acoplamiento suave y eficiente utilizando boronatos de vinilo.
Para permitir la formación de enlaces carbono-carbono con dos socios de acoplamiento.

Principales métodos:

Se utilizan boronatos de vinilo como reactivos de acoplamiento.
Se emplean condiciones de reacción suaves.
Facilitado el doble acoplamiento a través de enlaces carbono-carbono.

Principales resultados:

Se logró un acoplamiento exitoso de boronatos de vinilo.

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Published on: April 4, 2014

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

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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

Published on: March 20, 2014

Se ha demostrado la formación de enlaces carbono-carbono en condiciones suaves.

Mostró la capacidad de aparearse con dos compañeros.

Conclusiones:

Los boronatos de vinilo son reactivos eficaces para la formación de enlaces C-C suaves.
El método desarrollado ofrece un enfoque versátil para sintetizar moléculas complejas.