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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.1K
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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Halogenation of Alkenes02:46

Halogenation of Alkenes

15.8K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
15.8K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.5K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.5K
Halogens03:01

Halogens

18.5K
Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
18.5K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.2K
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...
8.2K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.3K

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Updated: Jul 17, 2025

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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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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Difluoromethylene insertion into fluoroalkyl copper complexes.

Yuyang Zhou1, Ryohei Doi1, Sensuke Ogoshi1

  • 1Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, 565-0871, Osaka, Japan. rdoi@chem.eng.osaka-u.ac.jp.

Chemical Communications (Cambridge, England)
|September 7, 2023
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel extended perfluoroalkyl-bridged compounds by inserting difluoromethylene units into copper complexes. These compounds feature diverse functional groups, enabling versatile applications in materials science.

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Area of Science:

  • Organometallic Chemistry
  • Fluorine Chemistry
  • Materials Science

Background:

  • Perfluoroalkyl compounds are crucial in materials science due to their unique properties.
  • Developing efficient synthetic routes for complex perfluoroalkyl structures remains a challenge.

Purpose of the Study:

  • To report a novel method for synthesizing extended perfluoroalkyl-bridged compounds.
  • To introduce diverse functional groups at both ends of the perfluoroalkyl chain.

Main Methods:

  • Insertion of a difluoromethylene unit into 1,1,2,2-tetrafluoro-2-arylethyl copper complexes.
  • One-pot synthesis utilizing aryl boronic acid esters.

Main Results:

  • Successfully synthesized extended perfluoroalkyl-bridged compounds with the general structure ArCF2CF2(CF2)nR.
  • Demonstrated the incorporation of various functional groups (arenes, halogens, alkyl, alkenyl, benzyloxycarbonyl) at the R position.
  • Achieved one-pot synthesis from readily available aryl boronic acid esters.

Conclusions:

  • The developed method provides efficient access to a new class of functionalized perfluoroalkyl-bridged compounds.
  • These compounds hold potential for applications in advanced materials and specialized chemical synthesis.
  • The one-pot approach simplifies the synthesis, making it more amenable for broader use.