Video Experimental Relacionado

Updated: Jun 16, 2026

[(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

La alquinilación directa catalizada por el cobre de los polifluoroarenos deficientes en electrones con alquinas

Ye Wei¹, Huaiqing Zhao, Jian Kan

¹State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.

Journal of the American Chemical Society

|February 6, 2010

Resumen

Este estudio introduce un nuevo método de alquinilación directa catalizada por cobre para los polifluoroarenos con déficit de electrones utilizando alquinas terminales. La reacción es eficiente bajo condiciones suaves, utilizando oxígeno como oxidante verde.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis es la catálisis.
Química del flúor Química del flúor

Sus antecedentes:

Los polifluoroarenos son bloques de construcción importantes en la ciencia de los materiales y la química medicinal.
Los métodos de funcionalización directa son muy deseables para una síntesis eficiente.
Las reacciones de alquilación introducen valiosos enlaces triples carbono-carbono.

Objetivo del estudio:

Desarrollar una nueva alquinilación directa catalizada por cobre de los polifluoroarenos con déficit de electrones.
Para explorar el alcance de la reacción con varios alquinos terminales.
Para lograr la transformación en condiciones suaves y respetuosas con el medio ambiente.

Principales métodos:

La catálisis del cobre.
La alquinilación directa es una alquinilación directa.
Oxidación con el O(2)

Principales resultados:

El éxito de la alquinización directa de los polifluoroarenos deficientes en electrones con diversas alquinas terminales.
La reacción procede eficientemente bajo condiciones suaves.
El oxígeno se empleó como un oxidante verde y rentable.

Conclusiones:

Se ha establecido una nueva ruta sintética para los polifluoroarenos sustituidos por alquinilo.
Este método ofrece una herramienta valiosa para acceder a complejas moléculas orgánicas fluoradas.
El uso de la catálisis del cobre y el oxidante O ((2) destaca un enfoque sostenible.

Más Videos Relacionados

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

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

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.

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.

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions generating free carboxylic acid...

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.