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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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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The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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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.
3.4K
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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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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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Pd(II)/PIDA-Enabled Migratory Triple Functionalization of Terminal Alkenes via a 1,2-C/Pd(IV) Dyotropic

Chen-Xu Liu1, Qian Wang1, Jieping Zhu1

  • 1Laboratory of Synthesis and Natural Products (LSPN), Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, Lausanne, 1015, Switzerland.

Angewandte Chemie (International Ed. in English)
|October 24, 2025
PubMed
Summary

This study introduces a novel palladium-catalyzed reaction for alkene functionalization. The process creates valuable 1,3-oxazine compounds by forming new carbon-carbon and carbon-oxygen bonds.

Keywords:
Dyotropic rearrangementHeterocycleHigh valent palladiumOxypalladationPIDA

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Palladium catalysis is crucial for modern organic synthesis.
  • Oxidative transformations using hypervalent iodine reagents are well-established.
  • Dyotropic rearrangements offer unique pathways for molecular construction.

Purpose of the Study:

  • To develop a novel Pd(II)-catalyzed migratory triple functionalization of terminal alkenes.
  • To synthesize 6-acetoxylated 5,6-dihydro-4H-1,3-oxazines.
  • To elucidate the reaction mechanism involving a Pd(II)/Pd(IV) catalytic cycle and a dyotropic rearrangement.

Main Methods:

  • Utilizing palladium(II) catalysis with homoallylic amides and phenyliodine(III) diacetate (PIDA).
  • Investigating the reaction pathway through mechanistic studies.
  • Characterizing the resulting 1,3-oxazine products.

Main Results:

  • A novel Pd(II)-catalyzed migratory triple functionalization of terminal alkenes was achieved.
  • 6-Acetoxylated 5,6-dihydro-4H-1,3-oxazines were synthesized in one step.
  • The mechanism involves oxypalladation, Pd(II) to Pd(IV) oxidation, and a 1,2-alkyl(aryl)/Pd(IV) dyotropic rearrangement.

Conclusions:

  • The reported dyotropic rearrangement in a Pd(II)/Pd(IV) system is unprecedented.
  • This transformation provides a new synthetic route to functionalized 1,3-oxazines.
  • The study expands the scope of palladium-catalyzed oxidative transformations.