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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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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.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.2K
Halogenation of Alkenes02:46

Halogenation of Alkenes

18.1K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
18.1K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

9.6K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
9.6K
Radical Halogenation: Thermodynamics01:34

Radical Halogenation: Thermodynamics

4.4K
The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
4.4K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.2K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Remote Fluorination and Fluoroalkyl(thiol)ation Reactions.

Fa-Guang Zhang1, Xue-Qi Wang1, Yin Zhou1

  • 1Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Frontiers Science Center for Synthetic Biology (Ministry of Education), and Tianjin Collaborative Innovation Center of Chemical Science & Engineering, Tianjin University, Tianjin, 300072, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 12, 2020
PubMed
Summary

This review covers advances in remote functionalization, enabling C-H bond transformations distant from existing groups. New strategies facilitate the synthesis of complex fluorinated compounds previously difficult to access.

Keywords:
1,5-hydrogen atom transferfluorinationfluoroalkyl(thiol)ationmetal migrationremote functionalization

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry

Background:

  • Remote functionalization allows C-H or C-C bond modification away from a functional group.
  • This is crucial for synthesizing complex molecules with precise modifications.

Purpose of the Study:

  • To review recent breakthroughs in remote fluorination, trifluoromethylation, difluoromethylation, trifluoromethylthiolation, and fluoroalkenylation.
  • To highlight strategies for controlling reactivity and selectivity in these remote transformations.

Main Methods:

  • Summarizes key strategies including undirected radical approaches, 1,5-hydrogen atom transfer, metal migration, distant directing groups, and ring-opening reactions.
  • Focuses on advancements in controlling distal selectivity and reactivity.

Main Results:

  • Several powerful strategies have emerged for remote C-H and C-C bond functionalization.
  • These methods enable predictable and unconventional transformations.

Conclusions:

  • The reviewed strategies facilitate the preparation of a wide range of difficult-to-access alkyl, aromatic, heteroaromatic, and complex fluorides.
  • Advances in remote functionalization offer new pathways for synthesizing valuable fluorinated organic compounds.