Video Experimental Relacionado

Updated: Sep 9, 2025

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

meta-Sal de diariliodonio sustituido habilitado Aryne 1,2,4'-Trifuncionalización

Lifeng Chu¹, Junjie Jiang¹, Limin Wang¹

¹Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, Department of Fine Chemistry and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.

Organic letters

|August 28, 2025

Resumen

Un nuevo método logra la trifuncionalización de las arinas utilizando sales de diariliodonio. Esta cascada de reacción forma enlaces C-N, C-S y para-selectivos C-C de manera eficiente.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

La química de aryne es crucial para la construcción de moléculas orgánicas complejas.
El desarrollo de métodos de funcionalización selectiva para las arinas sigue siendo un desafío importante en la síntesis orgánica.

Objetivo del estudio:

Desarrollar una nueva reacción en cascada para la trifuncionalización de 1,2,4 arinas.
Para lograr la formación secuencial de enlaces C-N, C-S y para-selectivo C-C en una sola operación sintética.

Principales métodos:

Se utilizan sales de diariliodonio meta sustituidas como precursores.
Se empleó una secuencia de reacción que implicaba un desplazamiento sigmatrópico [5,5] seguido de un reordenamiento tia-Fries.

Principales resultados:

Se logró con éxito la 1,2,4-trifuncionalización de las arinas.
Se demostró la formación secuencial de enlaces C-N y C-S.
Se ha logrado la formación de enlaces para-selectivos C-C en el anillo aromático no arino.

Conclusiones:

La reacción en cascada desarrollada ofrece una ruta eficiente a compuestos aromáticos trifuncionalizados complejos.
Este método proporciona una herramienta poderosa para los químicos sintéticos, permitiendo la construcción de arquitecturas moleculares intrincadas.

Más Videos Relacionados

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

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

Videos de Conceptos Relacionados

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,...

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.

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...

Acidity of 1-Alkynes

Acidity of 1-Alkynes

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

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...

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.