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Related Concept Videos

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.
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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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...
5.7K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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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.
10.7K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

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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.
10.5K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

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Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
4.4K
Crown Ethers02:36

Crown Ethers

6.3K
Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
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Related Experiment Video

Updated: Apr 15, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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Alkyl Aryl Ether Bond Formation with PhenoFluor.

Xiao Shen1, Constanze N Neumann, Claudia Kleinlein

  • 1Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA 02138 (USA) http://www.rittergroup.org.

Angewandte Chemie (International Ed. in English)
|March 25, 2015
PubMed
Summary

A new PhenoFluor-catalyzed reaction efficiently forms alkyl aryl ether bonds between phenols and alcohols. This method broadens substrate scope and tolerates functional groups, overcoming limitations of traditional ether synthesis.

Keywords:
CO bond formationMitsunobu reactionPhenoFluoralkyl aryl ethersfluorine

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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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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Related Experiment Videos

Last Updated: Apr 15, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

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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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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Ether bond formation is crucial in organic synthesis.
  • Conventional methods often face limitations with specific substrates and functional groups.

Purpose of the Study:

  • To develop a novel catalytic system for alkyl aryl ether synthesis.
  • To expand the scope and functional group tolerance in ether bond formation.

Main Methods:

  • Utilized PhenoFluor as a catalyst for the reaction between phenols and primary/secondary alcohols.
  • Investigated substrate scope and functional group compatibility.

Main Results:

  • Successfully developed a new alkyl aryl ether bond formation reaction.
  • Demonstrated broad substrate scope and tolerance for various functional groups.
  • Identified challenging substrates amenable to this new coupling method.

Conclusions:

  • PhenoFluor offers a distinct and effective approach to alkyl aryl ether synthesis.
  • The developed method overcomes limitations of conventional etherification processes.