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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

3.3K
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.
3.3K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.0K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
4.0K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.6K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.6K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.1K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.1K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.0K
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.
3.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.4K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
8.4K

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Updated: Nov 7, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Electrochemical Dehydrogenative C(sp2 )-H Amination.

Mahesh Puthanveedu1,2, Vladislav Khamraev2,3,4, Lukas Brieger5

  • 1Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Straße 11, 44227, Dortmund, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 1, 2021
PubMed
Summary

A new transition-metal-free direct electrolytic C-H amination method was developed. This efficient process uses an in situ generated electrolyte and an electrochemically generated nitrenium ion intermediate for C-H functionalization.

Keywords:
aminationcarbazoleelectrochemistryheterocyclesnitrenium ion

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Catalysis

Background:

  • Direct C-H amination is a crucial transformation in organic synthesis.
  • Traditional methods often rely on transition metal catalysts or stoichiometric oxidants, posing environmental and cost concerns.
  • Developing metal-free and efficient C-H amination strategies remains a significant challenge.

Purpose of the Study:

  • To develop a novel transition-metal-free direct electrolytic C-H amination protocol.
  • To demonstrate the utility of an electrochemically generated nitrenium ion intermediate.
  • To establish an efficient and simple method for both intramolecular and intermolecular C-H amination.

Main Methods:

  • Electrosynthesis was employed, eliminating the need for transition metal catalysts.
  • An in situ generated electrolyte was utilized to facilitate the reaction.
  • An electrochemically generated nitrenium ion intermediate was key to the C-H amination process.

Main Results:

  • A novel transition-metal-free direct electrolytic C-H amination was successfully developed.
  • The reaction proceeded efficiently under simple electrochemical conditions.
  • Both intramolecular and intermolecular C-H amination reactions were demonstrated with high efficacy.

Conclusions:

  • The developed electrosynthesis offers a sustainable and efficient alternative for C-H amination.
  • The use of an electrochemically generated nitrenium ion intermediate bypasses the need for traditional catalysts.
  • This method provides a simple and versatile approach for synthesizing valuable nitrogen-containing compounds.