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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
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...
2.1K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.7K
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...
1.7K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
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...
1.7K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.1K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.8K
Radical Formation: Elimination00:51

Radical Formation: Elimination

1.7K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
1.7K

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Radical-Mediated Trifunctionalization Reactions.

Qiang Zhang1, Xiaoming Ma2, Sanjun Zhi3

  • 1School of Chemistry and Life Sciences, Suzhou University of Science and Technology, 99 Xuefu Road, Suzhou 215009, China.

Molecules (Basel, Switzerland)
|August 10, 2024
PubMed
Summary

This review explores radical addition-initiated trifunctionalization reactions, enabling the construction of complex molecular scaffolds. These methods utilize synthetic radicals for sequential functionalizations of alkenes and alkynes.

Keywords:
additionalkenealkyneatom transfercyclizationgroup transferradicaltrifunctionalization

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Synthetic radicals are powerful tools for constructing molecular scaffolds.
  • Previous reviews covered various difunctionalization strategies.
  • Multifunctionalization remains an area for development.

Purpose of the Study:

  • To present radical addition-initiated trifunctionalization reactions.
  • To detail reaction pathways for alkenes, alkynes, and derivatives.
  • To expand the scope of synthetic radical chemistry.

Main Methods:

  • Radical addition to unsaturated systems (alkenes, alkynes).
  • Subsequent functionalization via group/hydrogen atom transfer, cyclization, or radical coupling.
  • Analysis of reaction mechanisms and scope.

Main Results:

  • Demonstration of trifunctionalization via radical addition initiation.
  • Identification of diverse pathways for sequential functionalization.
  • Construction of complex molecular architectures.

Conclusions:

  • Radical addition-initiated trifunctionalization offers a versatile approach.
  • These methods expand synthetic capabilities for complex molecule synthesis.
  • Synthetic radicals provide efficient routes to novel molecular scaffolds.