Video Experimental Relacionado

Updated: Sep 16, 2025

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

Acoplamiento cruzado entre ácidos arilborónicos y alquinas terminales en microgotas de agua

Sandeep Bose¹, Mohammad Mofidfar¹, Richard N Zare¹

¹Department of Chemistry, Stanford University, Stanford, California 94305, United States.

Journal of the American Chemical Society

|July 9, 2025

Resumen

Este estudio introduce una nueva reacción de acoplamiento cruzado sin catalizador en microgotas de agua, formando de manera eficiente enlaces C-C para sintetizar alquinas de arilo internas. Este enfoque de la química verde es adecuado para la preparación de medicamentos farmacéuticos.

Área de la Ciencia:

Química orgánica
Química ecológica
Ingeniería de reacción

Sus antecedentes:

La formación tradicional de enlaces C-C a menudo requiere condiciones duras y catalizadores.
El desarrollo de métodos sintéticos sostenibles es crucial para la protección del medio ambiente y la fabricación farmacéutica.

Objetivo del estudio:

Desarrollar un método suave y sin catalizadores para la formación de enlaces C-C.
Para sintetizar las alquinas de arilo internas utilizando microgotas de agua.
Para aclarar el mecanismo de reacción de este nuevo acoplamiento.

Principales métodos:

El electrospray de una mezcla de alquino terminal y ácido arilborónico en agua-acetonitrilo.
Utilizando la espectrometría de masas (MS) y la espectrometría de masas en tándem (MS2) para el análisis del producto.
Realizar estudios de reacción in situ y experimentos radicales para determinar el mecanismo.

Principales resultados:

Se obtienen los productos de reacción de acoplamiento C(sp2)-C(sp) en milisegundos.
Se han identificado como reactivos el fenilacetileno y el ácido 4-metoxifenilborónico.
Determinado el mecanismo de reacción a través de estudios detallados.

Conclusiones:

El método desarrollado proporciona una vía sostenible y ambientalmente benigna para la síntesis de alquinas arilo internas.
Este enfoque es adecuado para la preparación de bloques de construcción para medicamentos farmacéuticos.
Las microgotas de agua permiten la formación de enlaces C-C eficientes y libres de catalizadores en condiciones suaves.

Más Videos Relacionados

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

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

Videos de Conceptos Relacionados

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.

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

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.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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...