Video Experimental Relacionado

Updated: Feb 24, 2026

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Cicloadición azida-alquina catalizada por níquel para acceder a 1,5-disubstituidos 1,2,3-triazoles en el aire y el

Woo Gyum Kim¹, Mi Eun Kang¹, Jae Bin Lee¹

¹School of Energy and Chemical Engineering, Ulsan National Institute of Science and Technology (UNIST) , 50 UNIST-gil, Ulsan 44919, Republic of Korea.

Journal of the American Chemical Society

|August 18, 2017

Resumen

Un nuevo catalizador basado en níquel permite la síntesis eficiente de 1,5-disubstituidos 1,2,3-triazoles. Este método funciona en agua a temperatura ambiente, ofreciendo una ruta más ecológica y accesible para crear estas importantes estructuras químicas.

Área de la Ciencia:

Química orgánica
Catálisis
Química medicinal

Sus antecedentes:

Las cicloadiciones azida-alquina son reacciones clave para la síntesis de 1,2,3-triazoles.
Las reacciones catalizadas por cobre producen 1,4-regioisómeros, mientras que los 1,5-regioisómeros son difíciles de acceder, especialmente en condiciones acuosas suaves.
Los métodos existentes para los 1,5-regioisómeros a menudo requieren catalizadores sensibles o tienen un alcance de sustrato limitado.

Objetivo del estudio:

Desarrollar un sistema catalítico robusto para la síntesis de 1,5-disubstituidos 1,2,3-triazoles.
Para lograr esta síntesis en condiciones suaves, acuosas y ambientales.
Ampliar el alcance del sustrato para la formación de 1,5-triazol, incluidas las aplicaciones biomoleculares.

Principales métodos:

Utilizando un sistema catalítico compuesto de Cp2Ni y Xantphos.
Realización de la reacción de cicloadición azida-alquina tanto en solventes acuosos como orgánicos.
Conduciendo la reacción a temperatura ambiente.

Principales resultados:

Síntesis exitosa de 1,5-disubstituidos 1,2,3-triazoles con una amplia gama de sustratos, incluidos los compuestos alifáticos y aromáticos.
El sistema catalítico demuestra tolerancia al agua y al aire, funcionando eficazmente a temperatura ambiente.
El protocolo es simple, escalable y aplicable a la síntesis de triazoles que contienen carbohidratos y aminoácidos.

Conclusiones:

El sistema Cp2Ni/Xantphos proporciona un método eficiente y versátil para acceder a los 1,5-disubstituidos 1,2,3-triazoles.
Este protocolo supera las limitaciones de los métodos anteriores, permitiendo reacciones en condiciones suaves y acuosas.
La amplia aplicabilidad, incluidas las biomoléculas, pone de relieve el potencial de este nuevo sistema catalítico en diversas aplicaciones de síntesis química.

Más Videos Relacionados

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

Videos de Conceptos Relacionados

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

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...

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic S_N1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...

Preparation of Nitriles

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO₂ Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.