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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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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 Oxidation of Allylic and Benzylic Alcohols

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Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

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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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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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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.
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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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Radicalizing CO by Mononuclear Palladium(I).

Tim Bruckhoff1, Joachim Ballmann1, Lutz H Gade1

  • 1Anorganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 276, 69120, Heidelberg, Germany.

Angewandte Chemie (International Ed. in English)
|March 18, 2024
PubMed
Summary

A novel palladium(I) metalloradical was synthesized and characterized. This radical complex reacts with carbon monoxide and disulfide, forming new organometallic compounds.

Keywords:
T-shaped complexescarbonyl ligandsmetalloradicalspalladiumradicals

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Ligand-Mediated Nucleation and Growth of Palladium Metal Nanoparticles
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Area of Science:

  • Organometallic Chemistry
  • Radical Chemistry
  • Coordination Chemistry

Background:

  • Palladium(I) complexes are relatively rare and exhibit unique reactivity.
  • Stabilizing low-valent palladium species requires specific ligand design.

Purpose of the Study:

  • To synthesize and characterize a mononuclear palladium(I) d9 metalloradical.
  • To investigate the reactivity of this metalloradical with small molecules like carbon monoxide and disulfides.

Main Methods:

  • Synthesis of a palladium(I) complex using palladium chloride reduction or neopentyl complex homolysis.
  • Characterization via X-ray diffraction and Electron Paramagnetic Resonance (EPR) spectroscopy.
  • Theoretical modeling using Density Functional Theory (DFT) and ab initio methods.

Main Results:

  • A T-shaped palladium(I) d9 metalloradical stabilized by a carbazole-based PNP-ligand was successfully obtained.
  • The palladium(I) carbonyl complex was formed and structurally characterized.
  • EPR spectroscopy and theoretical calculations confirmed electron delocalization to the carbonyl carbon.
  • The metalloradical reacted with di(tert-butyl) disulfide, yielding a metallathioester via S-S cleavage and C-S bond formation.

Conclusions:

  • The study demonstrates the successful synthesis and characterization of a unique palladium(I) metalloradical.
  • The findings highlight the potential of such radical species in small molecule activation and C-S bond formation.