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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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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...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

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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...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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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.
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1.8K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
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:
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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.
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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...
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Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
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Terminal C(sp3)-H borylation through intermolecular radical sampling.

Miao Wang1, Yahao Huang1, Peng Hu1

  • 1Institute of Green Chemistry and Molecular Engineering, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China.

Science (New York, N.Y.)
|February 1, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a new photocatalytic method for selectively functionalizing terminal C(sp3)-H bonds in alkanes. The iron-catalyzed borylation process overcomes challenges in site-selective alkane transformations.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Photochemistry

Background:

  • Hydrogen atom transfer (HAT) is crucial for activating strong C(sp3)-H bonds in alkanes.
  • Site-selective functionalization of unbranched alkanes remains challenging due to similar C(sp3)-H bond strengths.

Purpose of the Study:

  • To develop a photocatalytic method for selective borylation of terminal C(sp3)-H bonds.
  • To address the challenge of site-selectivity in alkane functionalization.

Main Methods:

  • Iron-catalyzed intermolecular radical sampling.
  • Photocatalysis.
  • Mechanistic investigations.

Main Results:

  • Achieved selective borylation of terminal C(sp3)-H bonds in unbranched alkanes.
  • Demonstrated a reversible HAT process followed by selective carbon radical borylation.
  • Identified a potential role for a boron-sulfoxide complex in achieving high regioselectivity.

Conclusions:

  • The developed photocatalytic method offers a new route for selective alkane functionalization.
  • The findings advance the field of C-H bond activation and functionalization.