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Related Concept Videos

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 Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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.
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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.7K
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,...
3.7K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.5K
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 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...
4.0K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Related Experiment Video

Updated: Jul 16, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Ruthenium-Catalyzed Aminocarbonylation with Isocyanates Through Weak Coordinating Groups.

Elisa Y Lai1,2, Binbin Yuan2, Lutz Ackermann2,3

  • 1Medicinal Chemistry, Research and Early Development, Cardiovascular, Renal and Metabolism (CVRM), Biopharmaceuticals R&D, AstraZeneca, Gothenburg, Pepparedsleden1, 431 50, Mölndal, Sweden.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 22, 2023
PubMed
Summary

Researchers developed a mild ruthenium-catalyzed C-H aminocarbonylation method using isocyanates. This new protocol efficiently creates amide bonds in biologically relevant molecules under user-friendly conditions.

Keywords:
C−H activationamidationsdensity functional calculationshigh-throughput experimentationruthenium

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The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Medicinal Chemistry

Background:

  • Amide functional groups are crucial in biologically active molecules.
  • Mild synthetic methods for introducing amides are highly sought after.
  • Directed C-H functionalization offers efficient synthetic strategies.

Purpose of the Study:

  • To develop a mild and efficient protocol for directed C-H aminocarbonylation.
  • To utilize isocyanates as amidating agents in a ruthenium-catalyzed reaction.
  • To enable the synthesis of anthranilamide derivatives.

Main Methods:

  • Ruthenium-catalyzed C-H aminocarbonylation.
  • High-throughput experimentation (HTE) for reaction optimization.
  • Directed functionalization guided by Lewis basic groups (anilides, lactams, carbamates).

Main Results:

  • A mild, redox-neutral, and base-free protocol for C-H aminocarbonylation was established.
  • The reaction successfully synthesized anthranilamide derivatives.
  • The method demonstrated utility in large-scale synthesis and late-stage functionalization.

Conclusions:

  • The developed protocol provides a valuable method for synthesizing amide-containing compounds.
  • This approach offers a mild and efficient route to important molecular scaffolds.
  • The reaction's applicability in late-stage functionalization enhances its synthetic utility.