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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–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...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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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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Sulfur-Mediated Synthesis of Indole-Fused Medium-Sized Rings.

Yiwen Huang1, Chuang Lu1, Shilin Wang1

  • 1Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.

Organic Letters
|June 25, 2026
PubMed
Summary

This study presents a novel, transition-metal-free method for synthesizing indole-fused medium-sized rings in a single step. The innovative approach utilizes an interrupted Pummerer reaction followed by cyclization, offering a direct route from indole precursors.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Indole derivatives are crucial scaffolds in pharmaceuticals and materials science.
  • Efficient synthesis of complex indole-fused ring systems remains a challenge.
  • Developing transition-metal-free synthetic strategies is desirable for sustainability and cost-effectiveness.

Purpose of the Study:

  • To develop a novel, one-pot, transition-metal-free method for synthesizing indole-fused medium-sized rings.
  • To explore the scope and limitations of the new synthetic strategy.
  • To demonstrate the versatility of the method in accessing different ring sizes and substitution patterns.

Main Methods:

  • The synthesis involves an interrupted Pummerer reaction between indoles and activated cyclic sulfoxides.
  • The reaction proceeds via ring opening of intermediate sulfonium acetals, followed by cyclization.
  • Trifluoroacetic anhydride (TFAA) was used to activate the sulfoxides.

Main Results:

  • Indole-fused seven-membered rings were synthesized using TFAA-activated sulfoxides of five-membered N,S-acetals, with sulfur at the C-2 position of the indole.
  • Indole-fused eight-membered rings were obtained using TFAA-activated 1,3-dithiane (a six-membered S,S-acetal), with sulfur at the C-3 position of the indole.
  • The reaction provides direct access to functionalized indole-fused medium-sized rings.

Conclusions:

  • A novel and efficient transition-metal-free strategy for synthesizing indole-fused medium-sized rings has been established.
  • The method allows for controlled formation of seven- and eight-membered rings depending on the choice of cyclic sulfoxide.
  • This approach offers a valuable new tool for the construction of complex indole-containing molecules.