Video Experimental Relacionado

Updated: Jan 17, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Monodentate Transient Directing Group Enabled Distal C─H Bond Functionalization in Ferrocenecarboxaldehyde

Ashwini Dilip Dhumale¹, Devendra Parganiha¹, Shilpi Bhardwaj¹

¹Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, Madhya Pradesh, India.

Chemistry, an Asian journal

|January 14, 2026

Resumen

This study introduces a new method for distal C-H activation using palladium migration, facilitated by a transient directing group. This approach enables efficient heteroannular C-H functionalization of ferrocenecarboxaldehydes.

Área de la Ciencia:

Química organometálica
Catálisis
Química orgánica sintética

Sus antecedentes:

La activación distal C-H es crucial para la síntesis de moléculas complejas.
La migración de paladio en moléculas apiladas es una estrategia clave para la activación C-H.
Los grupos directores transitorios (TDG) pueden permitir la formación de paladaciclos para la migración.

Objetivo del estudio:

Desarrollar un método para la funcionalización distal C-H utilizando migración heteroanular de paladio.
Investigar el papel de los TDG monudentados y los ligandos en el ajuste fino de la migración de paladio.
Demostrar la eficacia de este método en ferrocenocarboxaldehídos.

Principales métodos:

Se utilizó un grupo director transitorio (TDG) monudentado y un ligando adicional.
Se investigaron las vías de migración de paladio a través de experimentos de control.
Se aplicó el método desarrollado para sintetizar ferrocenocarboxaldehídos funcionalizados.

Principales resultados:

Se logró con éxito la funcionalización distal heteroanular C-H de ferrocenocarboxaldehídos.
Se demostraron 23 ejemplos de esta novedosa funcionalización.
Se mostró el ajuste fino de la migración de paladio a través de TDG y la selección de ligandos.

Conclusiones:

La migración heteroanular de paladio habilitada por TDG monudentado es una estrategia viable para la activación distal C-H.
Este método ofrece una nueva ruta para la funcionalización de ferrocenocarboxaldehídos.
El enfoque proporciona una alternativa a las estrategias de activación C-H diseñadas por plantilla.

Palabras clave:

alquenilación activación distal C–H ferrocenos aceleración de ligandos catálisis de paladio

Más Videos Relacionados

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

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

Videos de Conceptos Relacionados

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...

Directing Effect of Substituents: ortho–para-Directing Groups

Directing Effect of Substituents: ortho–para-Directing Groups

Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...

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...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Directing Effect of Substituents: meta-Directing Groups

Directing Effect of Substituents: meta-Directing Groups

Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the...

meta-Directing Deactivators: –NO2, –CN, –CHO, –&NoBreak;CO2R, –COR, –CO2H

meta-Directing Deactivators: –NO₂, –CN, –CHO, –⁠CO₂R, –COR, –CO₂H

All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...