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Related Concept Videos

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: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
Preparation of Nitriles01:12

Preparation of Nitriles

One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta catalyst, high molecular...

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Updated: Jun 1, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Gold-catalyzed naphthalene functionalization.

Pedro J Pérez1, M Mar Díaz-Requejo, Iván Rivilla

  • 1Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al CSIC, Centro de Investigación en Química Sostenible (CIQSO), Universidad de Huelva, Campus de El Carmen 21007-Huelva, Spain.

Beilstein Journal of Organic Chemistry
|June 8, 2011
PubMed
Summary

Copper and gold catalysts featuring N-heterocyclic carbenes facilitate carbene group transfer reactions. The copper catalyst exclusively produces a cycloheptatriene derivative via the Buchner reaction, while the gold catalyst yields diverse products through C-H insertion or double bond addition.

Keywords:
carbene insertioncopper catalystsdiazoacetatesgold catalystsnaphthalene functionalizationselective insertion

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • N-heterocyclic carbenes (NHCs) are versatile ligands in organometallic chemistry.
  • Metal-NHC complexes are increasingly utilized as catalysts in organic transformations.
  • Carbene transfer reactions offer pathways for novel bond formations.

Purpose of the Study:

  • To investigate the catalytic activity of copper and gold NHC complexes in carbene transfer reactions.
  • To explore the influence of the metal center (Cu vs. Au) on reaction outcomes.
  • To characterize the products and byproducts of these catalytic processes.

Main Methods:

  • Synthesis and characterization of IPrCuCl and IPrAuCl complexes.
  • Catalytic transfer of carbene groups from ethyl diazoacetate derivatives.
  • Analysis of reaction products using spectroscopic techniques and chromatography.

Main Results:

  • The copper catalyst (IPrCuCl) exclusively mediated the Buchner reaction, yielding a cycloheptatriene derivative.
  • The gold catalyst (IPrAuCl) produced a mixture of products, including those from C-H insertion and double bond addition.
  • No carbene coupling byproducts were observed with either catalyst.

Conclusions:

  • The choice of metal center significantly dictates the selectivity of carbene transfer reactions.
  • Copper and gold NHC complexes offer distinct catalytic pathways for carbene functionalization.
  • These findings expand the scope of NHC-catalyzed reactions in organic synthesis.