Video Experimental Relacionado

Updated: Sep 10, 2025

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

Fluoración descarboxilada catalizada por el complejo de transferencia de carga que contiene piridina

Zhiyang Ma¹, Liang Zhang¹, Jinglan Wen¹

¹Institute of Green Chemistry and Molecular Engineering, GBRCE for Functional Molecular Engineering, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, China.

Organic letters

|August 20, 2025

Resumen

Un nuevo sistema de fotorreducción orgánica utiliza un complejo piridina-Selectfluor para la fluoración descarboxilada de ácidos carboxílicos impulsada por la luz visible. Este método convierte eficientemente varios ácidos alquilo carboxílicos en valiosos compuestos fluorados.

Área de la Ciencia:

Química orgánica
Catálisis por fotorreducción
Química de la fluoración

Sus antecedentes:

Las reacciones descarboxilativas son cruciales para la formación y la funcionalización de enlaces C-C.
La catálisis fotorredóxica ofrece un enfoque sostenible para las transformaciones orgánicas utilizando luz visible.
La fluoración selectiva sigue siendo un desafío importante en la química sintética.

Objetivo del estudio:

Desarrollar un nuevo sistema de descarboxilación por fotorreducción para la fluoración de ácidos alquilocarboxílicos.
Para utilizar un complejo de transferencia de carga como la especie catalítica para mejorar la reactividad.
Establecer un protocolo mediado por luz visible aplicable a diversos sustratos de ácido carboxílico.

Principales métodos:

Formación de un complejo de transferencia de carga entre los derivados de piridina y Selectfluor.
Irradiación con luz visible bajo condiciones básicas.
Aplicación a los ácidos alquilcarboxílicos primarios, secundarios y terciarios.

Principales resultados:

Fluoración descarboxilada exitosa de los ácidos alquilocarboxílicos.
Demostrado buen alcance del sustrato, incluyendo sustratos primarios, secundarios y terciarios.
El nuevo sistema catalítico funciona eficientemente bajo condiciones suaves.

Conclusiones:

El sistema de fotorreducción orgánica desarrollado proporciona una vía eficaz para la fluoración descarboxilada.
El enfoque complejo de transferencia de carga ofrece una estrategia única para activar los ácidos carboxílicos.
Esta metodología amplía el conjunto de herramientas para la introducción de fluor en moléculas orgánicas.

Más Videos Relacionados

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

Published on: June 10, 2021

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

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.

Acid Halides to Carboxylic Acids: Hydrolysis

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...

Acid Halides to Esters: Alcoholysis

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:

ortho–para-Directing Deactivators: Halogens

ortho–para-Directing Deactivators: Halogens

Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...

ortho–para-Directing Activators: –CH3, –OH, –&NoBreak;NH2, –OCH3

ortho–para-Directing Activators: –CH₃, –OH, –⁠NH₂, –OCH₃

All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...

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...