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Related Concept Videos

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

[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.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

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.
Cycloaddition Reactions: Overview01:16

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.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

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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Updated: May 30, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

A general method for copper-catalyzed arene cross-dimerization.

Hien-Quang Do1, Olafs Daugulis

  • 1Department of Chemistry, University of Houston, Houston, Texas 77204-5003, United States.

Journal of the American Chemical Society
|August 10, 2011
PubMed
Summary
This summary is machine-generated.

A new copper-catalyzed method enables regioselective cross-coupling of aromatic compounds. This advances synthetic chemistry by efficiently joining diverse arenes and heterocycles with broad functional group tolerance.

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[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Traditional cross-coupling reactions often require harsh conditions or large excesses of reactants.
  • Developing regioselective methods for joining aromatic compounds remains a key challenge in organic synthesis.

Purpose of the Study:

  • To develop a general and highly regioselective copper-catalyzed cross-coupling method for aromatic compounds.
  • To enable the coupling of diverse arenes and heterocycles with improved efficiency and functional group tolerance.

Main Methods:

  • A novel copper-catalyzed cross-coupling reaction utilizing iodine as an oxidant.
  • The method involves sequential iodination of one arene followed by C-H bond arylation of the second component.
  • Optimization of reaction conditions to achieve high regioselectivity and yield.

Main Results:

  • Successful cross-coupling of electron-rich arenes, electron-poor arenes, and various five- and six-membered heterocycles.
  • Demonstrated tolerance of common functional groups including esters, ketones, aldehydes, ethers, nitriles, nitro, and amines.
  • Achieved efficient coupling using a reduced ratio of coupling components compared to existing methods.

Conclusions:

  • A versatile and regioselective copper-catalyzed cross-coupling protocol has been established.
  • This method offers a significant advancement for the synthesis of complex aromatic and heteroaromatic molecules.
  • The broad substrate scope and functional group tolerance make this a valuable tool for synthetic chemists.