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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Nitriles to Ketones: Grignard Reaction00:57

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Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
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Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
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Radical Reactivity: Intramolecular vs Intermolecular01:33

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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Introduction
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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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Iron-Catalyzed Intermolecular N-H Insertion Using Acceptor-Acceptor Carbenes Derived from Iodonium Ylides.

Àlex Díaz-Jiménez1, Nil Insa-Carreras1, Anna Roglans1

  • 1Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, M. Aurèlia Capmany, 69, 17003 Girona, Catalonia, Spain.

Organic Letters
|July 15, 2025
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Summary

This study introduces an efficient iron-catalyzed method for N-H insertion into malonates using iodonium ylides. The reaction works for various amines under mild conditions, offering a new tool for amine functionalization.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • N-H insertion reactions are crucial for amine functionalization.
  • Developing efficient and mild catalytic methods remains an active area of research.

Purpose of the Study:

  • To report a general and efficient iron-catalyzed intermolecular N-H insertion method.
  • To functionalize malonate reagents at the intercarbonylic position using amines.

Main Methods:

  • Utilized iodonium ylides as electrophilic carbene precursors.
  • Employed simple iron(II) triflate as a catalyst.
  • Investigated the reaction with primary and secondary aromatic and aliphatic amines.

Main Results:

  • Achieved excellent yields for a wide range of amines.
  • Demonstrated the reaction proceeds under mild conditions (no inert atmosphere or anhydrous solvents required).
  • Observed remarkably short reaction times.

Conclusions:

  • The developed method provides a versatile and efficient route for amine functionalization via N-H insertion.
  • Mechanistic studies suggest a nonradical pathway involving an iron(II)-stabilized intermediate.