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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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...
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

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...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

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Published on: August 19, 2012

Surface functionalization using catalyst-free azide-alkyne cycloaddition.

Alexander Kuzmin1, Andrei Poloukhtine, Margreet A Wolfert

  • 1Department of Chemistry, Complex Carbohydrate Research Center, University of Georgia, Athens, 30602, United States.

Bioconjugate Chemistry
|October 23, 2010
PubMed
Summary
This summary is machine-generated.

This study demonstrates catalyst-free click chemistry for immobilizing molecules onto surfaces using aza-dibenzocyclooctyne (ADIBO). This efficient method works in aqueous solutions for various applications.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Materials Science

Background:

  • Catalyst-free click chemistry offers efficient molecular conjugation.
  • Surface immobilization is crucial for various applications, including diagnostics and materials science.
  • Copper-free click reactions provide biocompatible and efficient conjugation strategies.

Purpose of the Study:

  • To demonstrate the utility of catalyst-free azide-alkyne [3 + 2] cycloaddition for molecule immobilization.
  • To report an efficient synthesis of aza-dibenzocyclooctyne (ADIBO), a highly reactive cyclooctyne.
  • To describe methods for conjugating ADIBO with diverse molecules.

Main Methods:

  • Utilizing aza-dibenzocyclooctyne (ADIBO) for copper-free click reactions.
  • Derivatizing surfaces with ADIBO for azide-tagged substrate immobilization.
  • Anchoring ADIBO-conjugated molecules to azide-derivatized surfaces.
  • Employing PEG linkers for ADIBO conjugation.

Main Results:

  • Demonstrated successful immobilization of various molecules onto solid surfaces and microbeads.
  • Achieved efficient molecular conjugation in aqueous solutions under ambient conditions.
  • Reported the synthesis of ADIBO, the most reactive cyclooctyne for azide cycloaddition to date.
  • Showcased excellent reaction kinetics for both immobilization techniques.

Conclusions:

  • Catalyst-free azide-alkyne cycloaddition using ADIBO is a versatile and efficient method for surface immobilization.
  • The developed techniques are suitable for aqueous environments and proceed rapidly under mild conditions.
  • ADIBO represents a significant advancement in click chemistry for bioconjugation and materials functionalization.