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Videos de Conceptos Relacionados

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.2K
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...
4.2K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.1K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.1K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.5K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.5K
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...
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Una perspectiva sobre la funcionalización del enlace aromático C-H en etapa tardía

Li Zhang1, Tobias Ritter1

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany.

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|January 27, 2022
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La funcionalización en etapa tardía de los enlaces C-H ofrece una síntesis eficiente de moléculas complejas. Esta perspectiva evalúa los desafíos y las estrategias de C-H LSF aromáticos para la reactividad, la selectividad y el alcance.

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Área de la Ciencia:

  • Química orgánica
  • Química sintética

Sus antecedentes:

  • La funcionalización en etapa tardía de los enlaces C-H (C-H LSF) es una poderosa estrategia sintética.
  • C-H LSF permite una síntesis eficiente de moléculas complejas.
  • Sigue habiendo desafíos para lograr la selectividad en presencia de diversos grupos funcionales.

Objetivo del estudio:

  • Para evaluar el C-H LSF aromático.
  • Para discutir los desafíos actuales y las direcciones futuras en el campo.
  • Proporcionar información sobre la reactividad, la quimioselectividad, la selectividad del sitio y el alcance del sustrato.

Principales métodos:

  • Evaluación basada en la perspectiva de la literatura existente.
  • Análisis de las estrategias de funcionalización aromática C-H.
  • Discusión de los criterios clave: reactividad, quimioselectividad, selectividad del sitio y alcance del sustrato.

Principales resultados:

  • El C-H LSF aromático se enfrenta a desafíos significativos en cuanto a la selectividad.
  • Los métodos actuales requieren una cuidadosa consideración de las condiciones de sustrato y reacción.
  • Están surgiendo estrategias prometedoras para mejorar el control.

Conclusiones:

  • El C-H LSF aromático es un campo de rápido desarrollo con un potencial significativo.
  • Se necesita más investigación para superar los desafíos de la selectividad.
  • El crecimiento futuro radica en el desarrollo de métodos de funcionalización C-H más robustos y versátiles.