Video Experimental Relacionado

Updated: Sep 17, 2025

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

Reconstrucción de enlaces C-F catalizados por platino a través de la inserción de varias unidades para la migración

Yi-Bin Wang¹, Ming Chen¹

¹Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, 21 Gehu Road, Changzhou 213164, China.

Journal of the American Chemical Society

|June 30, 2025

Resumen

Los investigadores desarrollaron un nuevo método catalizado por platino para la formación remota de enlaces C-F. Esta estrategia utiliza difluoruros de gemas y heterociclos N para colocar con precisión los átomos de flúor hasta 19 enlaces en moléculas orgánicas.

Área de la Ciencia:

Química orgánica
Catálisis
Química del fluor

Sus antecedentes:

El control preciso de la colocación del átomo de flúor en la síntesis orgánica es un desafío significativo.
Los métodos existentes a menudo carecen de la capacidad de funcionalización remota.

Objetivo del estudio:

Desarrollar una nueva estrategia para la reconstrucción remota de enlaces C-F.
Para permitir la entrega intramolecular de flúor a través de distancias moleculares extendidas.

Principales métodos:

Inserción multiunidad catalizada por platino utilizando difluoruros de gemas y heterociclos N.
Investigación de un mecanismo de lanzadera Pt-F que incluye inserciones nucleófilas e intercambios de ligandos.
Estudio sistemático de la estequiometría del sustrato y de las investigaciones mecanicistas.

Principales resultados:

Entrega intramolecular exitosa de flúor en distancias de hasta 19 enlaces.
Alta regioselectividad y economía atómica en la formación de enlaces C-F.
Demostrar que las especies Pt-F coordinadas, y no el fluoruro libre, median la formación selectiva de enlaces C-F.

Conclusiones:

Se ha establecido una plataforma programable para la transferencia de flúor a largo alcance en la catálisis.
Desarrolló un plan para la edición remota de bonos CF.
Destacó las amplias implicaciones para el diseño molecular, el descubrimiento de fármacos y los materiales a base de flúor.

Más Videos Relacionados

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB

Published on: June 28, 2011

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.

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

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.

Base-Promoted α-Halogenation of Aldehydes and Ketones

Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base. The reaction begins with the abstraction of α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...