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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.7K
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.
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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.
7.3K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.4K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
7.4K
Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

7.7K
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.
7.7K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.4K
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...
2.4K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.6K
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,...
2.6K

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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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A Practical Method for Converting Benzyl Thioethers to Sulfonyl Fluorides.

Zhi-Hao Fan1, Eman Fayad2, Dalal Nasser Binjawhar3

  • 1School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, Wuhan 430070, People's Republic of China.

The Journal of Organic Chemistry
|November 17, 2025
PubMed
Summary

Researchers developed a new, cost-effective method using trichloroisocyanuric acid (TCCA) to convert benzyl sulfides into valuable sulfonyl fluorides. This efficient, one-pot process offers a simpler and greener route for synthesizing these important chemical building blocks.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Green Chemistry

Background:

  • Sulfonyl fluorides are versatile synthetic building blocks crucial in various chemical applications.
  • Developing efficient and economical synthetic routes for sulfonyl fluorides is an ongoing challenge in organic synthesis.

Purpose of the Study:

  • To introduce a novel, cost-effective, and efficient one-pot protocol for synthesizing sulfonyl fluorides.
  • To establish a transition-metal-free method for the conversion of benzyl sulfides to sulfonyl fluorides.

Main Methods:

  • A one-pot reaction protocol was developed utilizing trichloroisocyanuric acid (TCCA) as a key reagent.
  • The method involves the direct conversion of benzyl sulfides to sulfonyl fluorides under mild, transition-metal-free conditions.

Main Results:

  • The TCCA-mediated protocol demonstrated high efficiency in converting benzyl sulfides to diverse sulfonyl fluorides.
  • The reaction proceeds under mild conditions, showcasing operational simplicity and low cost.
  • The method is effective for a range of alkyl and (hetero)aryl sulfonyl fluoride constructions.

Conclusions:

  • A novel, efficient, and cost-effective TCCA-mediated one-pot method for synthesizing sulfonyl fluorides from benzyl sulfides has been established.
  • This transition-metal-free strategy offers a practical and synthetically useful approach to important sulfonyl fluoride motifs.
  • The developed protocol enhances the synthetic utility of sulfonyl fluorides through its operational simplicity and mild reaction conditions.