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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

2.4K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.4K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.9K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.9K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
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.
3.7K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.3K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
2.3K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.9K
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.
4.9K
Radical Formation: Overview01:03

Radical Formation: Overview

2.7K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.7K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.

Shishi Lin1, Shane D Lies1, Christopher S Gravatt1

  • 1Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.

Organic Letters
|December 30, 2016
PubMed
Summary
This summary is machine-generated.

This study introduces a new photocatalytic method using an arylsulfide group to create reactive alkene radical cations for cycloaddition reactions. This strategy overcomes limitations in photoredox catalysis, enabling access to unique chemical products.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Methodology

Background:

  • Photoredox catalysis enables unique chemical transformations.
  • Direct generation of alkene radical cations is thermodynamically challenging.
  • Existing methods have limitations in accessing certain product classes.

Purpose of the Study:

  • To develop a novel photocatalytic strategy for generating alkene radical cations.
  • To enable diverse cycloaddition reactions with electron-rich partners.
  • To circumvent thermodynamic limitations in photoredox reactions.

Main Methods:

  • Incorporation of an easily oxidized arylsulfide moiety into substrates.
  • Photocatalytic generation of alkene radical cations.
  • Reductive cleavage of the sulfide moiety in a traceless manner.

Main Results:

  • Successfully generated alkene radical cations via photocatalysis.
  • Achieved various cycloaddition reactions with electron-rich compounds.
  • Demonstrated traceless removal of the arylsulfide auxiliary.
  • Synthesized products not directly accessible by standard photoredox catalysis.

Conclusions:

  • The arylsulfide moiety acts as an effective oxidative "redox auxiliary".
  • This strategy provides a practical solution to thermodynamic barriers in photoredox reactions.
  • The method expands the scope of accessible products in photocatalytic synthesis.