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Related Concept Videos

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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...
Halogenation of Alkenes02:46

Halogenation of Alkenes

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.
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

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.
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

New developments in aromatic halogenation, borylation, and cyanation.

Di Qiu1, Fanyang Mo, Zhitong Zheng

  • 1Beining National Laboratory of Molecular Sciences, Peking University, China.

Chimia
|January 26, 2012
PubMed
Summary
This summary is machine-generated.

Researchers developed green synthesis methods for functionalized aromatics using gold, iron, and palladium catalysts. These efficient methods enable direct C-H functionalization and conversion of amines, advancing aromatic chemistry.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Catalysis

Background:

  • Traditional synthesis of functionalized aromatics often involves harsh conditions and multiple steps.
  • Developing sustainable and efficient methods for aromatic functionalization is crucial in organic synthesis.
  • Catalytic approaches offer pathways to milder reaction conditions and improved atom economy.

Purpose of the Study:

  • To present several novel green synthetic procedures for functionalized aromatic compounds.
  • To demonstrate the utility of different metal catalysts (Au, Fe, Pd) in promoting key transformations.
  • To highlight methods for direct C-H functionalization and efficient conversion of readily available precursors.

Main Methods:

  • Gold(III) chloride-catalyzed halogenation of aromatic compounds, including aryl boronates.
  • Iron(III) oxide-catalyzed direct aromatic C-H bond borylation.
  • Palladium-catalyzed direct cyanation of indoles and direct conversion of arylamines to pinacol boronates.

Main Results:

  • Successful synthesis of halogenated aromatics using a gold catalyst.
  • Efficient direct borylation of aromatic C-H bonds catalyzed by iron oxide.
  • Direct cyanation of indoles and conversion of arylamines to pinacol boronates achieved using palladium catalysis.

Conclusions:

  • The developed green procedures offer efficient and sustainable routes to valuable functionalized aromatic compounds.
  • These catalytic methods provide direct access to complex aromatic structures, minimizing waste and energy consumption.
  • The study showcases the versatility of gold, iron, and palladium catalysts in modern synthetic organic chemistry.