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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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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Hydrogen Bonds

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A hydrogen bond is formed when a weakly positive hydrogen atom already bonded to one electronegative atom (for example, the oxygen in the water molecule) is attracted to another electronegative atom from another polar molecule, such as water (H2O), hydrogen fluoride (HF), or ammonia (NH3). The huge electronegativity difference between the H atom (2.1) and the atom to which it is bonded (4.0 for an F atom, 3.5 for an O atom, or 3.0 for an N atom), combined with the very small size of an H atom...
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Radical Formation: Abstraction00:47

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The electron of an atom can be abstracted from a compound by a relatively unstable radical to generate a new radical of relatively greater stability. For example, an initiator which forms radicals by homolysis can abstract a suitable species like a hydrogen atom or a halogen atom from a compound to generate a new radical. This ability of radicals to propagate by abstraction is a crucial feature of radical chain reactions.
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Ionic Bonding and Electron Transfer02:48

Ionic Bonding and Electron Transfer

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Ions are atoms or molecules bearing an electrical charge. A cation (a positive ion) forms when a neutral atom loses one or more electrons from its valence shell, and an anion (a negative ion) forms when a neutral atom gains one or more electrons in its valence shell. Compounds composed of ions are called ionic compounds (or salts), and their constituent ions are held together by ionic bonds: electrostatic forces of attraction between oppositely charged cations and anions. 
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Electron Affinity03:07

Electron Affinity

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The electron affinity (EA) is the energy change for adding an electron to a gaseous atom to form an anion (negative ion).
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Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
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Rapid Iron(III)-Fluoride-Mediated Hydrogen Atom Transfer.

Chakadola Panda1, Lorna M Doyle1, Robert Gericke1,2

  • 1School of Chemistry, Trinity College Dublin, The University of Dublin, College Green, Dublin 2, Ireland.

Angewandte Chemie (International Ed. in English)
|September 28, 2021
PubMed
Summary

High-valent iron-fluoride complexes show promise as hydrogen atom transfer oxidants. Activation by acids dramatically enhances their reactivity for C-H activation, matching known potent oxidants.

Keywords:
biomimetic chemistryfluoride oxidanthigh-valent oxidantsnonheme ironproton-coupled electron transfer

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Area of Science:

  • Inorganic Chemistry
  • Organometallic Chemistry
  • Oxidation Chemistry

Background:

  • High-valent metal-fluoride species are predicted to be effective hydrogen atom transfer (HAT) oxidants due to the strong driving force from the H-F bond formation.
  • The development of novel oxidants is crucial for advancing catalytic C-H activation processes.

Purpose of the Study:

  • To synthesize and characterize novel high-valent iron-fluoride complexes.
  • To investigate the oxidative capabilities of these complexes in hydrogen atom transfer (HAT) reactions.
  • To explore the activation of these complexes using Lewis or Brønsted acids.

Main Methods:

  • Synthesis of a dimeric Fe(III)-F-Fe(III) complex (1) from a Fe(II) precursor and difluoroiodobenzene.
  • Activation of complex 1 with Lewis or Brønsted acids to form monomeric Fe(III) complexes (2).
  • Characterization of complexes 1 and 2 using various spectroscopic techniques (NMR, EPR, UV/Vis, FT-IR) and mass spectrometry.

Main Results:

  • A dimeric Fe(III)-F-Fe(III) complex (1) was successfully prepared.
  • Complex 1 exhibited sluggish oxidation activity but was readily activated by acids.
  • The activated monomeric Fe(III) complex (2) demonstrated high reactivity in oxidative C-H activation, comparable to potent Fe(III) and Fe(IV) oxidants.

Conclusions:

  • High-valent iron-fluoride complexes can serve as effective hydrogen atom transfer (HAT) oxidants.
  • Acid activation is a viable strategy to significantly enhance the reactivity of these iron-fluoride species.
  • The activated Fe(III) complexes represent a new class of potent reagents for oxidative C-H activation.