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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.7K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.2K
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.
3.2K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.2K
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...
4.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

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3.6K
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...
3.6K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
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.
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Controlling One- or Two-Electron Oxidation for Selective Amine Functionalization by Alternating Current Frequency.

Disni Gunasekera1, Jyoti P Mahajan1, Yanick Wanzi1

  • 1Department of Chemistry, Wayne State University, Detroit, Michigan 48202, United States.

Journal of the American Chemical Society
|May 27, 2022
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Summary
This summary is machine-generated.

Researchers developed a novel electrosynthesis method for selective amine oxidation using alternating current (AC) frequency. This approach generates key intermediates for arylation products and predicts optimal conditions, simplifying complex chemical reactions.

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Area of Science:

  • Organic Electrochemistry
  • Synthetic Organic Chemistry
  • Catalysis

Background:

  • Selective oxidation of tertiary amines is crucial for synthesizing valuable organic compounds.
  • Traditional methods often struggle with chemoselectivity, leading to undesired byproducts like iminium cations.
  • Optimizing reaction conditions for electrosynthesis typically involves time-consuming trial-and-error procedures.

Purpose of the Study:

  • To develop a novel electrosynthetic method for the selective one-electron oxidation of tertiary amines.
  • To generate α-amino radical intermediates efficiently, avoiding two-electron oxidation to iminium cations.
  • To establish a predictive method for optimizing alternating current (AC) electrolysis conditions.

Main Methods:

  • Electrosynthesis utilizing a unique alternating current (AC) frequency.
  • Cyclic voltammetry studies to identify an electrochemical descriptor.
  • Application of the descriptor to predict optimal AC frequencies for diverse amine substrates.

Main Results:

  • Achieved selective one-electron oxidation of tertiary amines to α-amino radical intermediates.
  • Facilitated easy access to arylation products by controlling AC frequency.
  • Identified a reliable electrochemical descriptor for predicting optimal AC frequencies, reducing optimization time.

Conclusions:

  • The developed AC electrolysis method offers a powerful alternative for solving chemoselectivity challenges in organic synthesis.
  • The predictive descriptor streamlines the optimization process for electrosynthetic reactions.
  • This work advances the field of electroorganic synthesis by providing a more efficient and predictable approach.