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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.9K
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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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.2K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.8K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
5.1K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Recent Advances in Copper-Based Solid Heterogeneous Catalysts for Azide-Alkyne Cycloaddition Reactions.

Noura Aflak1, Hicham Ben El Ayouchia1, Lahoucine Bahsis1,2

  • 1Laboratoire de Chimie Analytique et Moléculaire/LCAM, Faculté Polydisciplinaire de Safi, Université Cadi Ayyad, Safi 46030, Morocco.

International Journal of Molecular Sciences
|February 26, 2022
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Summary

Heterogeneous copper catalysts enable efficient copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. This approach simplifies catalyst recovery and reduces copper toxicity in biologically relevant compounds.

Keywords:
1,2,3-triazolesclick chemistrycoppercycloaddition reactionheterogeneous catalystsolid inorganic support

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Area of Science:

  • Green Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is a cornerstone of click chemistry, vital for complex systems and materials.
  • Homogeneous CuAAC reactions face challenges with catalyst removal and potential toxicity.
  • Heterogeneous catalysis offers advantages in catalyst recovery and reusability.

Purpose of the Study:

  • To review recent advancements in heterogeneous copper-based catalytic systems for CuAAC reactions.
  • To highlight the use of solid inorganic/organic hybrid supports in these systems.
  • To emphasize the benefits of heterogeneous CuAAC for bioconjugation and drug discovery.

Main Methods:

  • Review of literature on heterogeneous copper catalysts for CuAAC.
  • Focus on catalysts utilizing solid inorganic/organic hybrid supports.
  • Analysis of catalyst recovery, reusability, and copper removal techniques.

Main Results:

  • Heterogeneous copper catalysts facilitate efficient CuAAC reactions.
  • Solid hybrid supports enable easy catalyst separation via filtration.
  • This method significantly reduces residual copper in products, addressing toxicity concerns.

Conclusions:

  • Heterogeneous CuAAC catalysis provides a sustainable and practical route to 1,2,3-triazole compounds.
  • The facile removal of copper species is crucial for applications in medicinal chemistry and materials science.
  • This approach is scalable for industrial production of valuable triazole derivatives.