Video Experimental Relacionado

Updated: Apr 13, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Hidroarilación selectiva de éteres de vinilo catalizados por iridio a través de la activación de enlaces C-H

Yusuke Ebe¹, Takahiro Nishimura¹

¹Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.

Journal of the American Chemical Society

|May 1, 2015

Resumen

Los catalizadores de iridio permiten una hidroarilación eficiente de éteres de vinilo mediante la activación dirigida de enlaces C-H. Este método produce productos de adición con una excelente regioselectividad y un alto control de la rama.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
La activación de la C-H.

Sus antecedentes:

Las reacciones de hidroarilación son cruciales para la síntesis de moléculas orgánicas complejas.
La activación dirigida de enlaces C-H ofrece una estrategia sintética más eficiente al eludir los pasos de pre-funcionalización.
Los éteres de vinilo son versátiles bloques de construcción en la síntesis orgánica.

Objetivo del estudio:

Para desarrollar una nueva hidroariación catalizada por iridio de éteres de vinilo.
Para lograr altos rendimientos y selectividad a través de la activación dirigida de enlaces C-H de compuestos aromáticos.

Principales métodos:

Se utilizaron catalizadores de iridio para la reacción de hidroarilación.
Empleado activación dirigida de enlaces C-H de sustratos aromáticos.
Compuestos aromáticos reaccionados con éteres de vinilo en condiciones optimizadas.

Principales resultados:

Se obtienen altos rendimientos de los productos de adición deseados.
Se ha demostrado una alta regioselectividad en el proceso de hidroarilación.
Se observó un excelente control de la ramificación en la formación del producto.

Conclusiones:

La hidroariación catalizada por iridio a través de la activación dirigida de C-H es un método altamente efectivo.
El protocolo desarrollado proporciona una herramienta valiosa para la síntesis de compuestos aromáticos funcionalizados.
La alta selectividad ofrece ventajas para la síntesis de moléculas complejas.

Más Videos Relacionados

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Videos de Conceptos Relacionados

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.