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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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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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Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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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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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

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The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Fenolatos fotoinducidos por organocatálisis para la síntesis de isoindoloindolona con N-Iodobenzoyl Indoles

Annaram Thirupathi1, Su Bin Yoon1, Eun Joo Kang1

  • 1Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea.

The Journal of organic chemistry
|September 3, 2025
PubMed
Resumen

Un nuevo método organocatalítico sintetiza de manera eficiente las isoindoloindolonas mediante la catálisis de fenolatos fotoinducida. Este enfoque produce compuestos biológicamente significativos, incluidos los ligandos de los receptores de melatonina MT3 y 5-HT6.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química medicinal

Sus antecedentes:

  • Las isoindoloindolonas son compuestos heterocíclicos importantes con diversas actividades biológicas.
  • El desarrollo de rutas sintéticas eficientes y selectivas para estas moléculas es crucial para el descubrimiento de fármacos.

Objetivo del estudio:

  • Desarrollar una nueva metodología organocatalítica fotoinducida para la síntesis de isoindoloindolona.
  • Explorar el alcance del sustrato y la tolerancia del grupo funcional del método desarrollado.
  • Para sintetizar derivados de la isoindoloindolona biológicamente relevantes.

Principales métodos:

  • Catalización por transferencia de electrones inducida por la luz utilizando catalizadores de fenolatos.
  • Síntesis de las isoindoloindolonas a partir de los indoles de N-iodobenzoilo.
  • Investigaciones mecanicistas mediante espectroscopia UV-vis, amortiguación por fluorescencia y voltametría cíclica.

Principales resultados:

  • Se estableció un método organocatalítico eficiente para la síntesis de isoindoloindolona.
  • La metodología demostró un amplio alcance del sustrato, altos rendimientos y una excelente tolerancia del grupo funcional.
  • Los estudios mecánicos confirmaron una vía directa de transferencia de un solo electrón que involucra un catalizador de fenolato excitado.

Conclusiones:

  • La metodología organocatalítica de fenolatos fotoinducidos desarrollada proporciona una ruta eficiente hacia las isoindoloindolonas.
  • Este enfoque es valioso para sintetizar derivados biológicamente significativos, como la melatonina MT3 y los ligandos de los receptores 5-HT6.
  • El estudio ofrece información sobre el mecanismo catalítico, allanando el camino para un mayor desarrollo del catalizador.