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Related Concept Videos

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 Reactivity: Overview01:11

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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 Formation: Addition00:47

Radical Formation: Addition

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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...
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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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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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Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

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In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Copper-Catalyzed Radical Relay 1,3-Carbocarbonylation across Two Distinct C═C Bonds.

Nan-Nan Dai1, Yue-Jiao Lu1, Zhong-Qi Wu1

  • 1School of Materials Science and Chemical Engineering, Institute of Mass Spectrometry, Health Science Center, Ningbo University, Zhejiang 315211, China.

Organic Letters
|March 28, 2024
PubMed
Summary

This study introduces a novel radical relay method for 1,3-carbocarbonylation, efficiently forming multiple bonds across two separate carbon-carbon double bonds using inexpensive copper catalysts.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Catalysis

Background:

  • Radical relay reactions enable functionalization across remote chemical bonds.
  • Intermolecular assembly is crucial for complex molecule synthesis.

Purpose of the Study:

  • To report the first radical relay 1,3-carbocarbonylation of α-carbonyl alkyl bromides.
  • To achieve functionalization across two separate C═C bonds in a single step.

Main Methods:

  • Utilized a copper-catalyzed radical relay process.
  • Employed α-carbonyl alkyl bromides as substrates.
  • Investigated reaction mechanism via radical trapping and labeling experiments.

Main Results:

  • Achieved highly chemo- and regioselective 1,3-carbocarbonylation.
  • Formed two C(sp³)-C(sp³) bonds and one C═O bond concurrently.
  • Generated structurally diverse products under mild conditions.

Conclusions:

  • The developed radical relay offers an effective strategy for complex carbobicyclic synthesis.
  • The mild conditions and inexpensive catalyst facilitate broad applicability.
  • Mechanistic studies provide insights into the radical relay pathway.