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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.3K
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.
6.3K
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene

6.7K
Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the...
6.7K
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

5.5K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
5.5K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

7.3K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
7.3K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.1K
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.
16.1K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

3.1K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
3.1K

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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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Copper-Catalyzed Difluoroalkylation Reaction.

Dao-Qing Dong1, Shao-Hui Yang1, Pei Wu2

  • 1College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao 266109, China.

Molecules (Basel, Switzerland)
|December 11, 2022
PubMed
Summary

Recent advances in copper-catalyzed difluoroalkylation reactions are reviewed. These reactions, often involving the RCF2 radical, are classified into three distinct types based on their characteristics.

Keywords:
coppercoupling reactioncyclizationdifluoroalkylationmulticomponentradical

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Fluorination Chemistry

Background:

  • Copper-catalyzed reactions are crucial in modern organic synthesis.
  • Difluoroalkylation introduces two fluorine atoms into organic molecules, significantly altering their properties.
  • Understanding reaction mechanisms is key to developing new synthetic methodologies.

Purpose of the Study:

  • To review recent advancements in copper-catalyzed difluoroalkylation reactions.
  • To elucidate the proposed reaction mechanisms, particularly the role of the RCF2 radical.
  • To categorize existing copper-catalyzed difluoroalkylation reactions based on their unique features.

Main Methods:

  • Literature review of recent research articles.
  • Analysis of proposed reaction mechanisms.
  • Classification of reactions based on experimental characteristics and outcomes.

Main Results:

  • Recent progress in copper-catalyzed difluoroalkylation has been summarized.
  • The RCF2 radical is a commonly proposed intermediate in these transformations.
  • The reviewed reactions have been systematically classified into three distinct types.

Conclusions:

  • Copper-catalyzed difluoroalkylation reactions have seen significant development.
  • The classification provides a framework for understanding the diverse strategies in this field.
  • Further research can build upon these advances for novel difluoromethylation methods.