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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.
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...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

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...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

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.
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.

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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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A new, easily recyclable arylating agent based on a diphosphino-digold(I) complex.

Marianne Stol1, Dennis J M Snelders, Huub Kooijman

  • 1Organic Chemistry and Catalysis, Faculty of Science, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands.

Dalton Transactions (Cambridge, England : 2003)
|June 15, 2007
PubMed
Summary

New organogold(I) complexes efficiently transfer organic groups to titanium and palladium. The resulting gold byproducts precipitate, simplifying purification of the desired organometallic compounds.

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Synthesis and Calibration of Phosphorescent Nanoprobes for Oxygen Imaging in Biological Systems
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Synthesis and Calibration of Phosphorescent Nanoprobes for Oxygen Imaging in Biological Systems

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Synthesis and Calibration of Phosphorescent Nanoprobes for Oxygen Imaging in Biological Systems
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Synthesis and Calibration of Phosphorescent Nanoprobes for Oxygen Imaging in Biological Systems

Published on: March 3, 2010

Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Synthetic Chemistry

Background:

  • Organogold(I) complexes are valuable in synthesis.
  • Efficient transmetalation agents are crucial for creating new organometallic compounds.
  • Separation of byproducts can be challenging in organometallic reactions.

Purpose of the Study:

  • To synthesize novel digold(I) complexes for transmetalation reactions.
  • To investigate the transfer of anionic moieties to Ti(IV) and Pd(II) centers.
  • To evaluate the ease of separation of gold-containing byproducts.

Main Methods:

  • Synthesis of organogold(I) complexes, including digold and trinuclear species.
  • Transmetalation reactions with Ti(IV) and Pd(II) precursors.
  • Characterization using NMR spectroscopy and crystallographic analysis.
  • Filtration and solubility studies for byproduct separation.

Main Results:

  • Two digold(I) complexes, [(Au(NCN))2(dppbp)] and [(Au(Phebox))2(dppbp)], were synthesized.
  • These complexes effectively transferred NCN- and Phebox- ligands to Ti(IV) and Pd(II) respectively.
  • The gold byproduct, [(AuCl)2(dppbp)], precipitated quantitatively, facilitating separation.
  • A trinuclear gold(I) complex with high solubility was also reported.

Conclusions:

  • Digold(I) complexes serve as effective transmetalating agents.
  • The design of gold complexes can lead to easily separable byproducts.
  • The dimeric nature of the gold complex did not impede its transmetalating ability.