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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

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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.
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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 final...
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Electrophilic Aromatic Substitution: Overview01:16

Electrophilic Aromatic Substitution: Overview

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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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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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Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Palladium-Catalyzed Aromatic C-H Functionalizations Utilizing Electrochemical Oxidations.

Fumitoshi Kakiuchi1, Takuya Kochi1

  • 1Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa, 223-8522, Japan.

Chemical Record (New York, N.Y.)
|April 9, 2021
PubMed
Summary

Palladium-catalyzed electrochemical C-H functionalization offers a clean synthetic route. This study details novel halogenation, arylation, and coupling reactions using these efficient methods.

Keywords:
C−H activationC−H halogenationelectrochemical oxidationoxidative homocouplingpalladium catalyst

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Electrochemistry

Background:

  • Transition-metal-catalyzed reactions are vital for efficient organic synthesis.
  • Electrochemical methods offer sustainable and atom-economical alternatives.
  • C-H functionalization provides direct routes to complex molecules.

Purpose of the Study:

  • To explore palladium-catalyzed electrochemical C-H functionalization reactions.
  • To develop novel methods for C-H halogenation and arylation.
  • To showcase the versatility of these methods in organic synthesis.

Main Methods:

  • Palladium-catalyzed electrochemical C-H halogenation of arylpyridines and benzamides.
  • One-pot synthesis of teraryls via C-H iodination and Suzuki-Miyaura coupling.
  • Iodine-mediated oxidative homo-coupling of arylpyridines.

Main Results:

  • Successful C-H halogenation using HCl/HBr and I2 as halogen sources.
  • Efficient one-pot synthesis of teraryls achieved.
  • Demonstrated iodine-mediated oxidative homo-coupling of arylpyridines.

Conclusions:

  • Palladium-catalyzed electrochemical C-H functionalization is a powerful tool.
  • Developed methods offer efficient and selective routes to valuable organic compounds.
  • These reactions represent significant advancements in green chemistry and synthetic methodology.