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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.

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

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.

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

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Updated: Jul 12, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Advances in Selected Heterocyclization Methods.

Mónica Rivas¹, Vladimir Gevorgyan¹

¹Department of Chemistry and Biochemistry, The University of Texas at Dallas, 800 W. Campbell Road, Richardson, Texas 75080; Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, Texas 75390.

Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry

|October 25, 2023

Summary

This Account details a decade of research into synthesizing heterocycles. Key methods include transannulative reactions, reactive intermediate construction, and radical approaches for creating these vital chemical structures.

Keywords:

heterocycles radical heterocyclization transannulative heterocyclization transition metal catalyzed heterocyclization

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Last Updated: Jul 12, 2025

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Heterocycles are crucial structural motifs in pharmaceuticals and materials science.
Developing efficient synthetic routes to heterocycles remains a significant challenge in organic chemistry.

Purpose of the Study:

To summarize the group's advancements in heterocyclic synthesis over the past ten years.
To highlight key methodologies and strategies employed in the synthesis of complex heterocyclic compounds.

Main Methods:

Transannulative heterocyclizations
Construction of reactive intermediates for subsequent cyclization
Development of radical-based synthetic strategies

Main Results:

Demonstrated successful application of transannulative reactions for diverse heterocycle synthesis.
Established efficient pathways for generating reactive intermediates, enabling complex heterocycle construction.
Introduced novel radical approaches, expanding the scope of accessible heterocyclic scaffolds.

Conclusions:

The presented methodologies offer versatile and effective routes for synthesizing a wide range of heterocycles.
The advancements contribute to the broader field of synthetic organic chemistry, particularly in accessing important heterocyclic motifs.