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Videos de Conceptos Relacionados

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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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...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.1K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
6.1K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.3K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.3K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.2K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.3K
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...
6.3K

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Updated: Sep 10, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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O-benzilación quimioelectiva catalizada por Pd de los nucleófilos de la 2-quinolinona

Melissa Cadena1, Roberto Silva Villatoro1, Jyoti Shah Gupta1

  • 1The Max and Minnie Tomerlin Voelcker Laboratory for Organic Chemistry, Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.

ACS catalysis
|August 25, 2025
PubMed
Resumen
Este resumen es generado por máquina.

Desarrollamos un método catalizado por el paladio para la O-bencilación selectiva de 2-quinolinonas. Este enfoque proporciona 2-benciloxiquinolinas con un alto rendimiento y una excelente selectividad O:N utilizando un mínimo catalizador.

Palabras clave:
Las 2-quinolinonasPd-catálisisLos nucleófilos ambientesalquilación catalíticaSelectividad química

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química medicinal

Sus antecedentes:

  • Los nucleófilos ambidentes, como las 2-quinolinonas, presentan desafíos en la funcionalización selectiva.
  • El logro de la O-alquilación regioselectiva sobre la N-alquilación es crucial para la síntesis de derivados específicos de la quinolina.

Objetivo del estudio:

  • Desarrollar un método de O-benzilación altamente quimioselectivo para los nucleófilos de 2-quinolinona ambientes.
  • Explorar el ciclo catalítico e identificar los intermediarios clave en la reacción catalizada por el paladio.

Principales métodos:

  • Reacción de O-benzilación catalizada por el paladio.
  • Espectrometría de masas de alta resolución de inyección directa (DI-HRMS) para el seguimiento de las reacciones.
  • Espectroscopia de RMN 31P in situ para elucidar los intermedios de reacción.

Principales resultados:

  • O-bencilación exitosa de varias 2-quinolinonas sustituidas con altos rendimientos.
  • Se han demostrado excelentes selectividades O:N, hasta 100:1, favoreciendo la O-alquilación.
  • Se identificó un complejo de monóxido de fosfina Pd(II) eta1-bencilo como un intermediario catalítico clave.

Conclusiones:

  • Se ha establecido un método novedoso y eficiente catalizado por el paladio para la O-bencilación selectiva de las 2-quinolinonas.
  • El método ofrece una vía práctica para las 2-benciloxiquinolinas con alta regioselectividad y rendimiento.
  • Los conocimientos mecanicistas proporcionados por DI-HRMS e in situ 31P NMR avanzan en la comprensión de las reacciones catalizadas por Pd.