Video Experimental Relacionado

Updated: Mar 25, 2026

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

Funcionalización dual C-F, C-H a través de la fotocatálisis: acceso a los biaryles multifluorados

Sameera Senaweera¹, Jimmie D Weaver¹

¹Department of Chemistry, Oklahoma State University , Stillwater, Oklahoma 74078, United States.

Journal of the American Chemical Society

|February 19, 2016

Resumen

Ahora es más fácil sintetizar biarilos multifluorados. Este estudio introduce un método fotocatalítico para acoplar directamente los enlaces C-F con los enlaces C-H, ofreciendo una ruta versátil para moléculas fluoradas complejas.

Área de la Ciencia:

Química orgánica
Química sintética
Química del fluor

Sus antecedentes:

Los biarilos multifluorados son valiosos pero difíciles de sintetizar.
Los métodos tradicionales a menudo se basan en precursores prefuncionalizados y reacciones de acoplamiento cruzado.

Objetivo del estudio:

Desarrollar un método eficiente y directo para la síntesis de biarilos multifluorados.
Para explorar la funcionalización de enlaces fotocatalíticos C-F y C-H para la síntesis de biarilo.

Principales métodos:

Acoplamiento fotocatalítico de los perfluoroarenos (enlace C-F) con los arenos (enlace C-H).
Estrategia de funcionalización directa evitando los reactivos organometálicos tradicionales.

Principales resultados:

Se estableció una vía conveniente para los biarilos multifluorados.
El método demostró condiciones suaves, buena tolerancia funcional del grupo y amplio alcance.
Se logró el acceso a productos anti-Minisci de heterociclos básicos.
Construcción sistemática de biarilos con 2-5 enlaces carilo-F mediante fotocatálisis y química SNAr.

Conclusiones:

La funcionalización directa de C-F a través de la fotocatálisis ofrece una poderosa alternativa para sintetizar biarilos multifluorados complejos.
Este enfoque amplía las posibilidades sintéticas en la química del organofluoro.

Más Videos Relacionados

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

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.

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

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.

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.