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Related Concept Videos

Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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Updated: May 11, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
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Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron

Published on: August 12, 2019

Using Iron amides as Basic Reagents for Fluoroarene Metalation.

Jennifer Kuziola1, Eva Hevia2

  • 1Departement für Chemie und Biochemie (DCBP), Universität Bern, Freiestrasse 3, CH-3012, Bern, Switzerland. kuziolajennifer@gmail.com.

Chimia
|May 9, 2026
PubMed
Summary
This summary is machine-generated.

Iron(II) amides enable regioselective C-H functionalization of fluoroarenes, preserving C-F bonds. This study presents novel strategies using sodium ferrate and super basic iron amides for efficient fluoroarene ferration under mild conditions.

Keywords:
Bimetallic cooperativityDeprotonative metalationIron amidesSodium

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • Fluoroarenes are crucial building blocks in synthesis.
  • Regioselective C-H functionalization of fluoroarenes, maintaining C-F bonds, is challenging.

Purpose of the Study:

  • To develop novel methods for regioselective C-H functionalization of fluoroarenes.
  • To explore the utility of iron(II) amides in fluoroarene chemistry.

Main Methods:

  • Utilized iron(II) amides for C-H functionalization via Fe(II)-H exchange.
  • Investigated two strategies: sodium ferrate-mediated heterobimetallic cooperation and super basic iron amides (TMP-based).

Main Results:

  • Achieved regioselective mono- and di-ferration of diverse fluoroaromatic substrates.
  • Demonstrated efficient fluoroarene ferration under mild reaction conditions.
  • Showcased the effectiveness of both presented strategies.

Conclusions:

  • Iron(II) amides are effective catalysts for regioselective C-H functionalization of fluoroarenes.
  • Developed mild and efficient methods for fluoroarene ferration.
  • Highlighted the potential of heterobimetallic cooperation and super basic iron amides in C-F bond chemistry.