Video Experimental Relacionado
Updated: May 17, 2026
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
11:44
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
La activación del enlace metileno C(sp3)-H habilitado por ligando con un catalizador Pd(II)
Masayuki Wasa1, Kelvin S L Chan, Xing-Guo Zhang
1Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.
Journal of the American Chemical Society
|November 3, 2012
Resumen
Los investigadores desarrollaron un nuevo método catalizado por el paladio para la funcionalización de enlaces C-H. Este método instala de manera eficiente grupos arilo en las amidas utilizando un ligando de quinolina especializado.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Química Medicinal La Química Medicinal es el campo de la Química Medicinal.
Sus antecedentes:
- La activación de C-H catalizada por paladio es una herramienta poderosa en la síntesis orgánica.
- La funcionalización de los enlaces C(sp(3)) -H, particularmente en las amidas, sigue siendo un desafío.
- El desarrollo de métodos selectivos y eficientes para la funcionalización de C-H es crucial para el descubrimiento de fármacos y la ciencia de los materiales.
Objetivo del estudio:
- Desarrollar un nuevo método catalizado por paladio para la arilación directa de enlaces β-metileno C (((sp ((3)) -H en amidas.
- Explorar el papel del diseño de ligandos en el logro de la activación selectiva de C-H.
- Demostrar la amplia aplicabilidad del método desarrollado a varias amidas acíclicas y cíclicas.
Principales métodos:
- Utilizado en la catálisis del paladio (II).
- Empleó un ligando de quinolina mutuamente repulsivo y rico en electrones para dirigir la activación de C-H.
- Investigó el ajuste de ligandos para optimizar las condiciones de reacción y el alcance del sustrato.
- Aplicó el método a una amplia gama de sustratos acíclicos y cíclicos de amida.
Principales resultados:
- Se logró una inserción eficiente de Pd (II) en los enlaces C (sp) -H de β-metileno.
- Demostrado éxito en la arilación de amidas bajo condiciones suaves.
- Se identificó un ligando específico de quinolina que promueve una alta reactividad y selectividad.
- Mostró la eficacia del método en una variedad de estructuras de amida.
Conclusiones:
- El método desarrollado proporciona una nueva ruta para la funcionalización de enlaces C(sp(3)) -H desafiantes en amidas.
- El ligando de quinolina personalizado es clave para el éxito de la arylación catalizada por el paladio.
- Esta metodología tiene potencial para la síntesis simplificada de moléculas complejas y fármacos candidatos.
Más Videos Relacionados
Videos de Conceptos Relacionados
02:51Metal-Ligand Bonds
The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
01:11ortho–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...
02:17Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
00:57Cationic Chain-Growth Polymerization: Mechanism
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
01:23Properties of Organometallic Compounds
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.