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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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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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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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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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Ziegler–Natta Chain-Growth Polymerization: Overview01:17

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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...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

10.1K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
10.1K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
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.
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Accelerating Strain-Promoted Azide-Alkyne Cycloaddition Using Micellar Catalysis.

Grant I Anderton1, Alyssa S Bangerter1, Tyson C Davis1

  • 1Department of Chemistry, University of Utah, Salt Lake City, Utah 84112, United States.

Bioconjugate Chemistry
|June 10, 2015
PubMed
Summary
This summary is machine-generated.

Micellar catalysis significantly boosts bioorthogonal conjugation rates, particularly for hydrophobic molecules. This method enhances strain-promoted azide-alkyne cycloaddition (SPAAC) reactions, enabling faster and more efficient labeling of biomolecules.

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Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition
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Area of Science:

  • Chemical Biology
  • Bioconjugation Chemistry
  • Materials Science

Background:

  • Bioorthogonal conjugation reactions, including strain-promoted azide-alkyne cycloaddition (SPAAC), are crucial for site-specific biomolecule labeling.
  • SPAAC reaction rates are generally lower compared to copper-catalyzed azide-alkyne cycloaddition (CuAAC).
  • Improving SPAAC reaction kinetics is essential for broader applications in complex biological systems.

Purpose of the Study:

  • To investigate micellar catalysis as a strategy to accelerate SPAAC reactions.
  • To evaluate the effect of surfactants on reaction rates and selectivity between cyclooctynes and azides.
  • To demonstrate the applicability of micellar catalysis for both hydrophobic and hydrophilic SPAAC partners.

Main Methods:

  • Exploration of micellar catalysis using anionic and cationic surfactants.
  • Kinetic analysis of the reaction between benzyl azide and DIBAC cyclooctyne in the presence of surfactants.
  • Assessment of selectivity for hydrophobic versus hydrophilic azides.
  • Application of micellar catalysis to the reaction of a DIBAC-functionalized DNA sequence.

Main Results:

  • Anionic and cationic surfactants significantly enhanced SPAAC reaction rates, with up to 179-fold increase observed for benzyl azide and DIBAC cyclooctyne.
  • Surfactants provided substantial selectivity (up to 51-fold) for hydrophobic azides over hydrophilic ones.
  • A notable 11-fold rate enhancement was achieved for the reaction involving a DIBAC-functionalized DNA, demonstrating efficacy with hydrophilic biomolecules.

Conclusions:

  • Micellar catalysis is an effective strategy for accelerating SPAAC reactions, especially with hydrophobic reagents.
  • Surfactants can improve conjugation yields and reduce reaction times in bioorthogonal chemistry.
  • This approach broadens the utility of SPAAC for labeling diverse biomolecules, including those in aqueous environments.