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

Crossed Aldol Reactions: Overview

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Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.

Introduction to Electrophilic Addition Reactions of Alkenes

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The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...

Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

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Updated: Jul 15, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Divergent and Selective Light Alkene Cross-Coupling.

Zi-Chao Wang¹, Jia-Wen Zhang¹, Ming Joo Koh²

¹State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.

Angewandte Chemie (International Ed. in English)

|October 3, 2023

Summary

This summary is machine-generated.

This study introduces a novel nickel-catalyzed carbonickelation of light alkenes. The method efficiently converts abundant olefins into valuable chemicals like alkyl arenes and complex alkenes.

Keywords:

Carbonickelation Cross-Coupling Light Alkene N-Heterocyclic Carbene Nickel Catalysis

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Published on: April 4, 2014

Area of Science:

Organic Chemistry
Catalysis
Petroleum Chemistry

Background:

Light olefins are readily available petrochemical feedstocks.
Transforming olefins into high-value chemicals is a key challenge in synthesis.

Purpose of the Study:

To develop a regioselective method for upgrading light olefins.
To enable diverse functionalizations of alkenes using nickel catalysis.

Main Methods:

Regioselective carbonickelation of light alkenes.
In situ trapping with reductants, bases, or Grignard reagents.
Utilizing bulky N-heterocyclic carbene ligands on nickel catalysts.

Main Results:

Efficient 1,2-hydrofunctionalization and dicarbofunctionalization of alkenes.
Branched-selective Heck-type cross-coupling reactions.
Streamlined synthesis of alkyl arenes and complex alkenes.

Conclusions:

A modular and divergent platform for alkene upgrading was established.
The developed nickel-catalyzed strategy offers broad applications in medicinal chemistry and industry.