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

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

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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...
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Preparation of Amides01:29

Preparation of Amides

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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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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

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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.
3.6K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

8.0K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

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Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
6.1K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Imidazolylidene Cu(II) Complexes: Synthesis Using Imidazolium Carboxylate Precursors and Structure Rearrangement

Nathalie Ségaud1, Jonathan McMaster2, Gerard van Koten3

  • 1Department of Chemistry & Biochemistry , University of Bern , Freiestrasse 3 , 3012 Bern , Switzerland.

Inorganic Chemistry
|November 13, 2019
PubMed
Summary

A novel decarboxylation method synthesizes copper(II) complexes with N-heterocyclic carbenes (NHCs), even unstable ones. This technique avoids anaerobic conditions and offers versatile N-substituent and anion variations for copper complexes.

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Area of Science:

  • Organometallic Chemistry
  • Coordination Chemistry
  • Carbene Chemistry

Background:

  • Copper(II) complexes with N-heterocyclic carbenes (NHCs) are valuable in catalysis and materials science.
  • Traditional synthesis of Cu(II)-NHC complexes often requires stringent anaerobic conditions and struggles with unstable NHC ligands.

Purpose of the Study:

  • To develop a new, versatile synthetic methodology for preparing copper(II) complexes bearing monodentate N-heterocyclic carbenes (NHCs).
  • To enable the synthesis of Cu(II)-NHC complexes using NHCs that are unstable as free carbenes.
  • To investigate the influence of NHC N-substituents and copper-bound anions on complex stability and reactivity.

Main Methods:

  • In situ decarboxylation of imidazolium carboxylates to generate NHCs.
  • Reaction of generated NHCs with copper(II) salts (CuX2, X = OAc, Cl, Br, BF4, NO3).
  • Spectroscopic characterization including UV-vis and EPR spectroscopy, utilizing 13C labeling for hyperfine coupling analysis.

Main Results:

  • Successful synthesis of (NHC)CuX2 complexes via a decarboxylation route, which does not require anaerobic conditions.
  • Access to complexes with previously inaccessible unstable NHCs like N,N'-diisopropyl-imidazolylidene and N,N'-dimethyl-imidazolylidene.
  • Spectroscopic evidence confirmed the Cu-CNHC bond formation, with detailed analysis of carbene hyperfine coupling.
  • Demonstrated tunability of the complexes by varying NHC substituents and anions, influencing complex stability.
  • Observed structural rearrangements and ligand reorganization during recrystallization, including bond dissociation and disproportionation reactions, dependent on the anion X.

Conclusions:

  • The in situ decarboxylation of imidazolium carboxylates is an effective and versatile method for synthesizing Cu(II)-NHC complexes.
  • This methodology broadens the scope of accessible NHC ligands for copper coordination chemistry.
  • The stability and reactivity of the resulting complexes are significantly influenced by the electronic and steric properties of the NHC ligand and the nature of the counter-anion.