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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.8K
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,...
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Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

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In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday isolated...
14.0K
Basicity of Aromatic Amines01:18

Basicity of Aromatic Amines

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
8.1K
Stages of Infection01:26

Stages of Infection

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Stages of infection describe what happens to a susceptible host once a pathogen invades the human body. The stages of infection are incubation, prodromal, illness, stage of decline, and convalescence. The incubation stage is the period from exposure to a pathogen until symptoms start. The infected person is unaware of impending illness as the pathogens grow and multiply within the body. The duration may vary depending on the type of infection. The incubation period of measles averages ten to...
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Stages of General Anesthesia01:22

Stages of General Anesthesia

1.7K
Various sedation levels offer significant advantages in facilitating procedural interventions for patients undergoing medical or invasive surgical procedures. These levels span from anxiolysis to general anesthesia, providing a spectrum of sedative effects to cater to specific patient needs. Anxiolysis reduces anxiety and is achieved through minimal sedation, enabling patients to remain awake and responsive while feeling more at ease during the procedure. This level can benefit minor...
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Stages of Sleep01:22

Stages of Sleep

1.4K
Sleep progresses through distinct stages, each characterized by specific brain wave patterns and physiological responses ranging from wakefulness to stages of non-rapid eye movement, known as non-REM, to rapid eye movement, referred to as REM. Understanding these stages helps in recognizing how sleep supports various bodily and cognitive functions.
Before sleep begins, in wakefulness, the brain exhibits primarily beta waves, which are high in frequency and low in amplitude, indicating alertness...
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Video Experimental Relacionado

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Bioluminescence Imaging to Detect Late Stage Infection of African Trypanosomiasis
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Oxigenación aromática C-H en etapa tardía

Jonas Börgel1, Lalita Tanwar1, Florian Berger1

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

Journal of the American Chemical Society
|November 14, 2018
PubMed
Resumen

Desarrollamos un nuevo método para la formación de enlaces aromáticos oxidativos, cruciales para la síntesis de metabolitos de fármacos. Este enfoque ofrece una alta tolerancia de grupo funcional y permite bloquear los puntos calientes metabólicos mediante la instalación de enlaces C-F.

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Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Descubrimiento de drogas

Sus antecedentes:

  • Los métodos sintéticos para la formación de enlaces aromáticos oxidativos C-O son limitados.
  • La formación de enlaces aromáticos C-O es importante para la síntesis de metabolitos de fármacos.
  • La funcionalización en etapa tardía es clave en el descubrimiento y desarrollo de fármacos.

Objetivo del estudio:

  • Desarrollar una nueva metodología para la formación de enlaces C-O en etapas tardías de las arenas.
  • Proporcionar acceso a los metabolitos humanos potenciales de los productos farmacéuticos.
  • Para permitir el bloqueo de los puntos calientes metabólicos utilizando enlaces C-F.

Principales métodos:

  • Se utiliza el peróxido de bis (metanesulfonilo) como reactivo.
  • Formación de enlaces aromáticos oxidativos en las arenas.
  • Tolerancia y quimioselectividad del grupo funcional investigadas.

Principales resultados:

  • Se ha logrado una nueva formación de enlaces C-O en etapa tardía de arenas.
  • Se ha demostrado una excelente tolerancia del grupo funcional a sustratos altamente funcionalizados.
  • Mesilatos de arilo generados como precursores de metabolitos de fármacos y para la instalación de enlaces C-F.

Conclusiones:

  • El método desarrollado es valioso para sintetizar metabolitos humanos potenciales.
  • La metodología permite bloquear los puntos calientes metabólicos mediante la instalación de enlaces C-F.
  • Una interacción de transferencia de carga puede explicar la quimioselectividad de la reacción.