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Related Concept Videos

Redox Reactions01:24

Redox Reactions

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Oxidation-reduction or redox reactions involve the transfer of electrons from one molecule or atom to another. When an atom gains an electron, another atom must lose an electron, meaning oxidation and reduction must occur together. Since the redox occurs in pairs, the atom that gets oxidized is also called the reducing agent or reductant, and the atom that is reduced is also called the oxidizing agent or oxidant. A straightforward way to remember the definitions of oxidation and reduction is...
50.9K
Redox Reactions01:27

Redox Reactions

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Redox reactions are vital biochemical processes that underpin energy metabolism in cells. These reactions involve the transfer of electrons between molecules, occurring in tandem as oxidation and reduction. Oxidation refers to the loss of electrons, while reduction denotes their gain. This coupling ensures the seamless flow of electrons through metabolic pathways. For example, in bacterial metabolism, glucose undergoes oxidation to carbon dioxide, while oxygen is simultaneously reduced to...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

3.2K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

1.9K
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...
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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A copper-mediated oxidative N-cyanation reaction.

Fan Teng1, Jin-Tao Yu, Yan Jiang

  • 1Changzhou University, School of Petrochemical Engineering, Jiangsu Province Key Laboratory of Fine Petrochemical Engineering, Changzhou 213164, P. R. China. shchengjiang@163.com.

Chemical Communications (Cambridge, England)
|June 21, 2014
PubMed
Summary

This study introduces a new copper-catalyzed N-cyanation method for secondary amines using copper cyanide and oxygen as a clean oxidant. The reaction efficiently forms new carbon-nitrogen bonds, advancing cyanation chemistry.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-nitrogen (C-N) bond formation is crucial in synthesizing pharmaceuticals and materials.
  • Cyanation reactions are vital for introducing nitrile groups, which are versatile functional groups in organic synthesis.
  • Developing efficient and sustainable methods for C-N bond formation and cyanation remains an active area of research.

Purpose of the Study:

  • To develop a novel copper-promoted N-cyanation method for aliphatic secondary amines.
  • To utilize a clean and readily available oxidant, molecular oxygen (O2), in the cyanation process.
  • To explore the scope and applicability of the developed method with various amine substrates.

Main Methods:

  • Copper-catalyzed oxidative coupling reaction.
  • Utilizing copper cyanide (CuCN) as the cyanation reagent.
  • Employing molecular oxygen (O2) as the terminal oxidant.

Main Results:

  • Efficient N-cyanation of aliphatic secondary amines was achieved using CuCN and O2.
  • The reaction demonstrated good functional group tolerance, working well with sulfoximines and 1,1,3,3-tetramethylguanidine.
  • This method represents a significant advancement in C-N bond formation and cyanation reactions.

Conclusions:

  • A novel and efficient copper-promoted N-cyanation of secondary amines has been established.
  • The use of O2 as a clean oxidant highlights the sustainability of the developed protocol.
  • This methodology offers a valuable tool for constructing C-N bonds and synthesizing cyano-containing compounds.