Video Experimental Relacionado

Updated: May 13, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

La conversión catalizada por el rodio de los furanos en pirroles altamente funcionalizados

Brendan T Parr¹, Samantha A Green, Huw M L Davies

¹Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.

Journal of the American Chemical Society

|March 13, 2013

Resumen

Un nuevo método sintetiza pirroles funcionalizados utilizando iminocarbenos y furanos estabilizados con rodio. Esta reacción produce de manera eficiente pirroles trisubstituidos a través de un mecanismo de anulación [3+2] y apertura de anillos.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química Heterocíclica La Química Heterocíclica es una de las más conocidas.
La catálisis es la catálisis.

Sus antecedentes:

Los pirroles son compuestos heterocíclicos vitales que se encuentran en numerosos productos naturales y farmacéuticos.
La síntesis eficiente de pirroles altamente funcionales sigue siendo un desafío en la química orgánica.

Objetivo del estudio:

Desarrollar una nueva ruta sintética para pirroles altamente funcionales.
Para explorar la reactividad de los iminocarbenos estabilizados con rodio con derivados de furano.

Principales métodos:

Reacción de los iminocarbenos estabilizados con rodio con varios furanos.
Utilizando una estrategia de anulación [3+2].
Caracterización de los intermedios y productos de reacción.

Principales resultados:

Síntesis exitosa de pirroles trisubstituidos.
Formación de productos intermedios hemiaminos bicíclicos.
Demostración de una secuencia de apertura de anillo de anulación en tándem.

Conclusiones:

El método desarrollado proporciona una vía eficiente a las estructuras de pirrolo complejas.
Las reacciones catalizadas por el rodio ofrecen una herramienta versátil para la síntesis heterocíclica.
Este enfoque expande la utilidad sintética de los iminocarbenos y los furanos.

Más Videos Relacionados

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[(DPEPhos)(bcp)Cu]PF₆: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Videos de Conceptos Relacionados

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.

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.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the bromine molecule...