Video Experimental Relacionado

Updated: Apr 23, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Funcionalización del enlace C(sp(2)) -H catalizado por el hierro con compuestos de organoboron

Rui Shang¹, Laurean Ilies, Sobi Asako

¹Department of Chemistry, School of Science, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Journal of the American Chemical Society

|October 1, 2014

Resumen

Este estudio introduce un método de funcionalización C-H catalizado por hierro para acoplar diversos sustratos con compuestos organoboron. La reacción se lleva a cabo a través de un intermediario organohierro (III), crucial para la activación del enlace C-H y el acoplamiento eficiente.

Área de la Ciencia:

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

Sus antecedentes:

La funcionalización C-H es una estrategia clave en la síntesis orgánica.
El desarrollo de sistemas catalíticos eficientes para la activación de C-H sigue siendo un desafío importante.
Los compuestos de organoboron son socios de acoplamiento versátiles.

Objetivo del estudio:

Desarrollar una nueva reacción de funcionalización C-H catalizada por hierro.
Para permitir el acoplamiento de varios sustratos aromáticos, heteroaromáticos y olefínicos.
Para utilizar compuestos organoboron como socios de acoplamiento en condiciones suaves.

Principales métodos:

Funcionalización dirigida C-H catalizada por el hierro.
Condiciones de la reacción de acoplamiento oxidativo.
Utilizando sustratos aromáticos, heteroaromáticos y olefínicos.
Empleando compuestos de alquenilo y boro de arilo.
Investigando el papel de un promotor de sales de zinc.

Principales resultados:

Acoplamiento exitoso de diversos sustratos con compuestos de organoboron.
Demostración de las condiciones de reacción oxidativa leve.
Identificación de un intermediario orgánico de hierro.
Elucidación del mecanismo de activación del enlace C-H.
Confirmación del papel crucial de las sales de zinc en el ciclo catalítico.

Conclusiones:

La reacción catalizada por hierro desarrollada ofrece una nueva ruta para la funcionalización C-H.
El intermediario organohierro (III) es clave para el proceso de activación del enlace C-H.
Las sales de zinc son esenciales para facilitar la transferencia de grupos orgánicos en el ciclo catalítico.

Más Videos Relacionados

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

Videos de Conceptos Relacionados

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...