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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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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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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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[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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Pericyclic Reactions: Introduction01:17

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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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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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Mechanism Reevaluation and Reaction Development in Rhodium-Catalyzed Cycloaddition of gem-Difluorinated

Yaxin Zeng1, Han Gao2, Le Zhang1

  • 1West China School of Public Health and West China Fourth Hospital, State Key Laboratory of Biotherapy, Sichuan University, Chengdu, China.

Angewandte Chemie (International Ed. in English)
|April 15, 2026
PubMed
Summary
This summary is machine-generated.

This study reveals a new reaction pathway for rhodium-catalyzed cycloadditions involving gem-difluorinated cyclopropanes. The mechanism involves dual C-C/C-F bond activation, challenging previous interpretations and opening doors for novel synthetic strategies.

Keywords:
(3 + 2) cycloadditionC–F bond reconstructionallylationgem‐difluorinated cyclopropanesrhodium catalysis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Fluorine Chemistry

Background:

  • Transition-metal-catalyzed cycloadditions are key for complex molecule synthesis.
  • Rhodium-catalyzed (3+2) cycloaddition of gem-difluorinated cyclopropanes (gem-DFCPs) with olefins was previously studied.
  • The initial mechanistic interpretation involved a conventional cycloaddition pathway.

Purpose of the Study:

  • To re-evaluate the mechanism of the Rh-catalyzed (3+2) cycloaddition of gem-DFCPs.
  • To uncover the precise reaction pathway and intermediates involved.
  • To provide a revised mechanistic framework for future reaction development.

Main Methods:

  • Detailed mechanistic interrogation using control experiments.
  • Density Functional Theory (DFT) calculations to model reaction pathways.
  • Analysis of bond activation events, including C-C and C-F bonds.

Main Results:

  • The cycloaddition proceeds through a previously unrecognized pathway.
  • Dual C-C and C-F bond activation is involved.
  • The mechanism includes fluoroallylic substitution, carbocation-mediated cyclization, and fluoride transfer.

Conclusions:

  • The established mechanism for this cycloaddition is revised.
  • A new understanding of dual C-C/C-F bond activation in catalysis is presented.
  • This work inspires the design of novel synthetic methodologies utilizing gem-DFCPs.