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Related Concept Videos

Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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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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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.2K
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.
5.2K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

9.0K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
9.0K
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
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.7K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.7K

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Updated: Sep 27, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Benzyl thioether formation merging copper catalysis.

Bing Xu1,2, Ying Lin1,2, Yang Ye1,2

  • 1School of Pharmacy, Hangzhou Normal University Hangzhou Zhejiang 311121 PR China yangye@hznu.edu.cn.

RSC Advances
|April 15, 2022
PubMed
Summary
This summary is machine-generated.

A new copper-catalyzed reaction efficiently creates benzyl thioethers from alcohols and thiols. This mild method offers a selective way to form carbon-sulfur bonds.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Thioether synthesis is crucial in organic chemistry.
  • Developing efficient and selective methods for C-S bond formation is an ongoing challenge.

Purpose of the Study:

  • To develop a novel copper-catalyzed thioetherification reaction.
  • To synthesize benzyl thioethers from readily available starting materials under mild conditions.

Main Methods:

  • Utilized copper(II) triflate (Cu(OTf)2) as a Lewis acid catalyst.
  • Employed a variety of primary, secondary, and tertiary benzyl alcohols and thiols.
  • Conducted the reaction under mild and easy-to-operate conditions.

Main Results:

  • Achieved moderate to excellent yields of benzyl thioethers.
  • Demonstrated efficient preparation of a diverse range of thioethers.
  • Exhibited exceptional chemoselectivity in the C-S bond formation.

Conclusions:

  • The developed copper-catalyzed reaction is a highly effective method for synthesizing benzyl thioethers.
  • The reaction proceeds via a Lewis-acid-mediated SN1-type mechanism involving in situ generated carbocations.
  • This protocol offers a practical and selective approach to thioether synthesis.