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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.2K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.2K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
12.1K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

4.2K
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.
4.2K
Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

47.8K
sp3d and sp3d 2 Hybridization
47.8K
Bonding in Metals02:32

Bonding in Metals

51.8K
Metallic bonds are formed between two metal atoms. A simplified model to describe metallic bonding has been developed by Paul Drüde called the “Electron Sea Model”. 
51.8K

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Light-Induced Palladium(IV)-Carbon Bond Homolysis.

Linda De Marchi1, Maxime Tricoire1, Luca Demonti1

  • 1LCM, CNRS, École Polytechnique, Institut Polytechnique de Paris, Route de Saclay, Palaiseau 91120, France.

Journal of the American Chemical Society
|October 27, 2025
PubMed
Summary
This summary is machine-generated.

Researchers synthesized unusually stable palladium(IV) alkyl complexes using a Cp*2Yb(bipym) fragment. These complexes exhibit novel light-induced Pd-C bond homolysis, generating alkyl radicals for new chemical reactions.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles
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Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles

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Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles
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Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Photochemistry

Background:

  • Palladium chemistry, especially Pd(0)/Pd(II) cycles, is crucial for cross-coupling reactions, enabling C-X bond cleavage and C-C bond formation.
  • The reactivity and stability of Pd(IV) alkyl complexes are less understood due to their inherent instability, limiting their synthetic applications.

Purpose of the Study:

  • To synthesize and characterize unusually stable Pd(IV) alkyl complexes.
  • To investigate novel reactivities of these stable Pd(IV) complexes beyond classical reductive elimination.
  • To explore the potential of light-induced C-Pd bond homolysis for radical generation.

Main Methods:

  • Synthesis of novel Pd(IV) alkyl complexes stabilized by a Cp*2Yb(bipym) fragment.
  • Characterization using X-ray diffraction, solid-state magnetism, and 1H NMR spectroscopy.
  • Photochemical studies (370 nm irradiation) and mechanistic investigations using Density Functional Theory (DFT) and Electron Paramagnetic Resonance (EPR) spectroscopy.

Main Results:

  • Successfully synthesized and characterized stable Pd(Alkyl)4 fragments, Cp*2Yb(bipym)Pd(Me)3(R), with room temperature half-lives exceeding 17 hours.
  • Demonstrated the first instance of light-induced Pd(IV)-C bond homolysis, generating alkyl radicals.
  • Observed unique reactions including methyl radical coupling with the bipym ligand or formation of free methyl radicals upon irradiation.

Conclusions:

  • The Cp*2Yb(bipym) fragment imparts significant stability to Pd(IV) alkyl complexes, enabling detailed reactivity studies.
  • Light-induced homolysis of Pd(IV)-C bonds offers a novel pathway for generating alkyl radicals under mild conditions.
  • These findings open new avenues in palladium catalysis and photoredox chemistry.