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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

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Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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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...
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Synthesis and Decomposition Reactions02:17

Synthesis and Decomposition Reactions

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Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes. 
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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Silver and gold-catalyzed multicomponent reactions.

Giorgio Abbiati1, Elisabetta Rossi1

  • 1Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica "A. Marchesini", Università degli Studi di Milano, Via Venezian, 21 - 20133 Milano, Italy.

Beilstein Journal of Organic Chemistry
|March 8, 2014
PubMed
Summary

This review explores silver and gold compounds as soft Lewis acids and σ-activators. It highlights their roles in redox catalysis and multicomponent reactions, showcasing recent advancements in gold-mediated processes.

Keywords:
A3-couplinggoldmulticomponent reactionssilver

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Area of Science:

  • Organometallic Chemistry
  • Catalysis

Background:

  • Silver and gold compounds primarily function as soft, carbophilic Lewis acids.
  • Their application as σ-activators is less frequently documented.
  • Recent literature shows increasing interest in gold(I)/gold(III) redox catalytic systems.

Purpose of the Study:

  • To review the multifaceted roles of silver and gold in chemical transformations.
  • To emphasize their function as Lewis acids and σ-activators.
  • To highlight their utility in multicomponent reactions, particularly those involving gold redox catalysis.

Main Methods:

  • Literature review of silver and gold-mediated reactions.
  • Analysis of catalytic systems, including Au(I)/Au(III) redox cycles.
  • Examination of applications in multicomponent reaction strategies.

Main Results:

  • Silver and gold salts/complexes exhibit significant Lewis acidity, particularly towards soft and carbophilic substrates.
  • Evidence for their use as σ-activators is growing.
  • Gold-based redox catalysis is emerging as a powerful tool for synthetic transformations.

Conclusions:

  • Silver and gold complexes are versatile reagents with diverse catalytic capabilities.
  • Their application in multicomponent reactions offers efficient synthetic pathways.
  • Further exploration of gold redox catalysis is warranted for novel synthetic methodologies.