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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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Iodometry and iodimetry are analytical methods used to determine the concentration of oxidizing or reducing agents using iodine. In iodometric titrations, the oxidizing analyte solution is usually acidified and treated with an excess of iodide ions, which generates an equivalent amount of iodine in equilibrium with triiodide. The released iodine is subsequently titrated directly against a standardized reducing agent. As the dilute iodine color becomes pale yellow, a few drops of freshly...
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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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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...
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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.
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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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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Dioxoiodane Compounds as Versatile Sources for Iodine(I) Chemistry.

Kilian Muñiz1,2, Belén García1, Claudio Martínez1

  • 1Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 14, 2016
PubMed
Summary

New electrophilic iodine(I) reagents, R4N[I(O2CAr)2], are synthesized and stable. These novel compounds function effectively in various reactions, particularly in the vicinal iodooxygenation of alkenes.

Keywords:
alkenesdifunctionalizationiodineoxidationsynthetic methods

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Materials Science

Background:

  • Electrophilic iodine reagents are crucial in organic synthesis.
  • Development of stable and versatile iodine(I) reagents remains an active area of research.
  • Existing reagents often suffer from limited stability or scope.

Purpose of the Study:

  • To report the synthesis, isolation, and characterization of novel electrophilic iodine(I) reagents.
  • To investigate the stability and structural features of these new compounds.
  • To evaluate the performance of these reagents in various organic transformations, focusing on alkene iodooxygenation.

Main Methods:

  • General synthesis of R4N[I(O2CAr)2] compounds.
  • Isolation and purification techniques.
  • Characterization using methods including X-ray analysis.
  • Evaluation in 47 different vicinal iodooxygenation reactions of alkenes.

Main Results:

  • Successful synthesis and isolation of air- and moisture-stable iodine(I) reagents.
  • Structural characterization confirmed the novel nature of these compounds with anionic stabilizers.
  • Demonstrated effective performance as electrophilic reagents with electron-rich substrates.
  • Detailed study of performance in 47 vicinal iodooxygenation reactions revealed key reagent features.

Conclusions:

  • Conceptually new, stable iodine(I) reagents have been developed.
  • These reagents exhibit predictable reactivity as electrophilic species.
  • The study provides valuable insights into the application of these novel reagents in organic synthesis, particularly for alkene functionalization.