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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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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.3K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Reactions at the Benzylic Position: Halogenation01:11

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Related Experiment Video

Updated: Dec 24, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent.

Li-Jun Qiu1, Dan Liu1, Ke Zheng1

  • 1State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin, China.

Frontiers in Chemistry
|April 8, 2020
PubMed
Summary

A novel iodine(III) reagent, 1-Benzoyloxy-1,2-benziodoxol-3-(1H)-one (IBA-OBz), facilitates efficient dipeptide synthesis from diverse amino acids. This method also enables solid-phase peptide synthesis, including unprotected leu-enkephalin.

Keywords:
DFT calculationsIBA-OBzhypervalent iodine(III) reagentpeptidesolid-phase peptide synthesis (SPPS)

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Biochemistry

Background:

  • Peptide synthesis is crucial for drug discovery and development.
  • Traditional peptide synthesis methods can be complex and require protecting groups.
  • Development of efficient and mild peptide coupling reagents is an ongoing area of research.

Purpose of the Study:

  • To explore the utility of 1-Benzoyloxy-1,2-benziodoxol-3-(1H)-one (IBA-OBz) as a reagent for peptide synthesis.
  • To investigate the application of the IBA-OBz/(4-MeOC6H4)3P system in both solution-phase and solid-phase peptide synthesis.
  • To elucidate the mechanism of the peptide bond formation reaction using computational methods.

Main Methods:

  • Solution-phase synthesis of dipeptides using IBA-OBz and (4-MeOC6H4)3P with standard and sterically hindered amino acids.
  • Solid-phase peptide synthesis (SPPS) of leu-enkephalin using the IBA-OBz/(4-MeOC6H4)3P system.
  • Density functional theory (DFT) calculations to investigate the reaction mechanism and identify the rate-limiting step.

Main Results:

  • Successful synthesis of dipeptides from a range of amino acids, including sterically hindered ones, using the IBA-OBz/(4-MeOC6H4)3P system.
  • Demonstrated applicability of the reagent system for solid-phase peptide synthesis, yielding unprotected leu-enkephalin.
  • DFT calculations identified the nucleophilic attack of 4-dimethylaminopyridine (DMAP) onto IBA-OBz as the rate-limiting step.

Conclusions:

  • IBA-OBz is a versatile and effective reagent for both solution-phase and solid-phase peptide synthesis.
  • The developed method offers a mild and efficient approach for synthesizing peptides, including unprotected peptides.
  • Understanding the reaction mechanism provides insights for further optimization of iodine(III)-mediated peptide coupling reactions.