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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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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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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

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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 anion...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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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

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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...
1.9K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.1K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Updated: Jun 14, 2025

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C-H functionalization enabled by multiple isocyanides.

Mingchun Gao1, Shaohang Lu1, Bin Xu1,2,3

  • 1Department of Chemistry, Affiliated Nantong Hospital of Shanghai University (The Sixth People's Hospital of Nantong), Shanghai Engineering Research Center of Organ Repair, Innovative Drug Research Center, School of Medicine, Shanghai University, Shanghai 200444, China. xubin@shu.edu.cn.

Chemical Society Reviews
|September 4, 2024
PubMed
Summary
This summary is machine-generated.

This review highlights the power of using multiple isocyanides in C-H functionalization reactions. These methods offer efficient ways to build complex molecules for drug discovery and materials science.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology

Background:

  • Isocyanides are versatile building blocks in organic synthesis.
  • Multi-component reactions (MCRs) and tandem reactions extensively utilize isocyanides.
  • C-H functionalization offers atom economy and synthetic efficiency.

Purpose of the Study:

  • To review C-H functionalization reactions involving multiple isocyanides.
  • To discuss the mechanistic aspects of these transformations.
  • To showcase the utility in pharmaceutical chemistry and materials science.

Main Methods:

  • Review of literature on isocyanide-based C-H functionalization.
  • Analysis of reaction types and mechanistic pathways.
  • Highlighting synthetic applications and potential.

Main Results:

  • Detailed overview of various C-H functionalization reactions enabled by multiple isocyanides.
  • Discussion of mechanistic rationale behind these reactions.
  • Demonstration of the value in constructing complex molecules.

Conclusions:

  • C-H functionalization with multiple isocyanides is a powerful synthetic strategy.
  • This approach provides efficient access to diverse molecular architectures.
  • Significant potential exists for applications in drug discovery and materials science.