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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
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Radical Reactivity: Electrophilic Radicals01:02

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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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 Reactivity: Nucleophilic Radicals01:16

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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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Radicals: Electronic Structure and Geometry01:07

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
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Radical Formation: Elimination00:51

Radical Formation: Elimination

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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...
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Switchable Radical Carbonylation by Philicity Regulation.

Bin Lu1, Minghao Xu2, Xiaotian Qi2

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This study introduces a photoredox catalysis strategy for switchable single and double carbonylation reactions. This method precisely controls the formation of amides and α-ketoamides from simple starting materials.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Photochemistry

Background:

  • Carbonylation reactions are crucial for synthesizing carbonyl compounds using carbon monoxide (CO).
  • Existing methods often struggle to control single versus double carbonylation pathways for diverse products from simple precursors.

Purpose of the Study:

  • To develop a novel photoredox catalysis strategy for switchable single and double carbonylation reactions.
  • To enable controlled synthesis of amides and α-ketoamides from amine coupling partners.

Main Methods:

  • Utilizing photoredox catalysis to modulate amine reactivity.
  • Employing single-electron transfer-oxidation to generate nitrogen radical cations.
  • Controlling reaction pathways via the addition of 4-dimethylaminopyridine (DMAP) to switch between single and double carbonylation.

Main Results:

  • Achieved switchable radical carbonylation reactions with excellent selectivity.
  • Successfully synthesized valuable amides and α-ketoamides under mild conditions (room temperature).
  • Demonstrated versatility with various amine nucleophiles.

Conclusions:

  • The developed photoredox strategy offers a controlled and versatile approach to carbonylation.
  • The method allows for the selective synthesis of single or double carbonylation products by adjusting reaction conditions.
  • Mechanistic insights were gained through experimental and computational studies.