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Cycloaddition Reactions: Overview

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.

Cycloaddition Reactions: MO Requirements for Thermal Activation

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.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Preparation of 1° Amines: Azide Synthesis

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...

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

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Updated: Jan 10, 2026

Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition

Efficient and Site-specific Antibody Labeling by Strain-promoted Azide-alkyne Cycloaddition

Published on: December 23, 2016

Linker-Engineered Tyrosine-Azide Coatings for Stable Strain-Promoted Azide-Alkyne Cycloaddition (SPAAC)

Suho Park^1,2, Himani Bisht^1,2, Jiwoo Park³

¹Department of Chemistry and Chemistry, Institute for Functional Materials, Pusan National University, Busan 46241, Republic of Korea.

|November 27, 2025

Summary

This summary is machine-generated.

Researchers developed a stable, substrate-independent azide film using melanin-inspired coatings for surface chemistry. This biocompatible platform enables strain-promoted azide-alkyne cycloaddition (SPAAC) for antifouling and cell surface engineering applications.

Keywords:

melanin-inspired coatings metal-free clickable coatings soft lithography strain-promoted azide–alkyne cycloaddition (SPAAC)tyrosine–azide derivatives

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Published on: July 28, 2022

Area of Science:

Bioconjugation Chemistry
Materials Science
Surface Chemistry

Background:

Strain-promoted azide-alkyne cycloaddition (SPAAC) is a powerful bioconjugation tool but limited in surface applications due to unstable azide films.
Developing substrate-independent azide films that withstand SPAAC reactions is crucial for advancing surface chemistry.

Purpose of the Study:

To create a stable, substrate-independent azide film for surface-based SPAAC reactions.
To investigate melanin-inspired coatings based on tyrosine-azide derivatives for improved film stability and SPAAC compatibility.

Main Methods:

Synthesized tyrosine-azide derivatives with varying linker lengths and hydrophilicity.
Utilized tyrosinase-mediated oxidation to form azide-presenting films.
Assessed film stability during SPAAC with dibenzocyclooctyne (DBCO) ligands.
Evaluated antifouling properties via methoxypolyethylene glycol (mPEG) immobilization and protein adsorption resistance.
Demonstrated surface patterning using soft lithography (MIMIC, µCP).

Main Results:

Identified Tyr-3-N3 as optimal, forming stable azide films that retained integrity during SPAAC.
Achieved efficient mPEG immobilization, resulting in excellent antifouling performance.
Successfully patterned proteins using MIMIC and µCP techniques.
Demonstrated broad applicability across various substrates, including living cells, with maintained cell viability.

Conclusions:

Established a novel, substrate-independent, and biocompatible coating platform for SPAAC functionalization.
The developed melanin-inspired films offer enhanced stability and antifouling properties.
This platform supports diverse applications in biosensing, antifouling coatings, and cell surface engineering.