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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

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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...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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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,...
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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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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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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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Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Fluorine transfer to alkyl radicals.

Montserrat Rueda-Becerril1, Claire Chatalova Sazepin, Joe C T Leung

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|February 11, 2012
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A novel method for selective alkyl fluorination using N-fluorobenzenesulfonimide as a fluorine source for alkyl radicals has been developed. This breakthrough offers a safer, more versatile approach to synthesizing fluorine-containing compounds for pharmaceuticals.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Methodology

Background:

  • The demand for fluorine-containing pharmaceuticals drives the need for advanced synthetic technologies.
  • Conventional fluorination methods often employ ionic fluorine sources (F(-) or F(+)).
  • Radical fluorination strategies are limited by the scarcity of safe atomic fluorine (F(•)) sources.

Purpose of the Study:

  • To develop a new, safe, and effective method for the selective fluorination of alkyl radicals.
  • To expand the synthetic toolbox for introducing fluorine into organic molecules, particularly for pharmaceutical applications.

Main Methods:

  • Utilized N-fluorobenzenesulfonimide as a fluorine transfer agent.
  • Applied the method to a diverse range of alkyl radicals: primary, secondary, tertiary, benzylic, and heteroatom-stabilized.
  • Performed computational calculations to explore potential reagent modifications and reaction conditions.

Main Results:

  • Successfully achieved broad applicability in alkyl radical fluorination.
  • Demonstrated the efficacy of N-fluorobenzenesulfonimide as a fluorine source for various radical types.
  • Computational analysis identified promising fluorine-containing ionic reagents for polar media.

Conclusions:

  • The developed radical alkyl fluorination approach offers a powerful new synthetic transformation.
  • This method provides a valuable alternative to traditional multi-step syntheses.
  • Future work may involve expanding the methodology to polar reaction environments using ionic reagents.