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Related Concept Videos

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

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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...
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.4K
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene01:17

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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...
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Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

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5.5K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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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.
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Related Experiment Video

Updated: Jun 9, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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C-H Insertion from Isolable Copper Benzylidenes.

Erika Amemiya1, Shao-Liang Zheng1, Theodore A Betley1

  • 1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society
|October 23, 2024
PubMed
Summary
This summary is machine-generated.

Researchers isolated stable copper carbene complexes, demonstrating their ability to insert into C-H bonds. This breakthrough clarifies their role in catalysis and potential deactivation pathways.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Carbene Chemistry

Background:

  • Copper catalysts are widely used for C-H bond functionalization.
  • The key copper carbene intermediate has remained elusive and uncharacterized.

Purpose of the Study:

  • To synthesize and characterize novel copper carbene complexes.
  • To investigate the reactivity of these isolated copper carbenes in C-H insertion reactions.

Main Methods:

  • Synthesis of copper benzylidenes using sterically encumbered dipyrrin ligands.
  • Structural characterization of the isolated copper carbene complexes.
  • Stoichiometric studies of C-H insertion and olefin cyclopropanation reactions.

Main Results:

  • Isolation and structural characterization of stable copper(I) carbene adducts.
  • Demonstration of intramolecular C(sp³)-H insertion into the ligand backbone.
  • Observation of intermolecular C-H insertion into ethereal and allylic bonds.
  • Catalytic C-H insertion achieved with a modified ligand.

Conclusions:

  • Isolated copper carbenes exhibit Fischer carbene-like reactivity.
  • These findings provide direct evidence for copper carbenes as catalytic intermediates.
  • Understanding these intermediates is crucial for optimizing copper-catalyzed reactions and preventing catalyst deactivation.