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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 anion...
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

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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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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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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...
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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Electrochemical Benzylic C-H Functionalization with Isocyanides.

Shanyu Tang1, Régis Guillot1, Laurence Grimaud2

  • 1Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Saclay, CNRS, 91405 Orsay, France.

Organic Letters
|March 14, 2022
PubMed
Summary

This study introduces an electrochemical method for direct carbamoylation and cyanation of benzylic C(sp3)-H bonds using isocyanides. This approach yields valuable structures found in pharmaceuticals, avoiding harsh conditions and prefunctionalized starting materials.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Medicinal Chemistry

Background:

  • Benzylic C(sp3)-H bonds are important structural motifs in biologically active molecules.
  • Direct functionalization of these bonds remains a significant synthetic challenge.
  • Existing methods often require prefunctionalized substrates or harsh reaction conditions.

Purpose of the Study:

  • To develop a novel electrochemical method for direct carbamoylation and cyanation of benzylic C(sp3)-H bonds.
  • To utilize isocyanides as versatile building blocks in this transformation.
  • To access valuable α-aryl acetamide and α-aryl acetonitrile derivatives.

Main Methods:

  • Direct electrochemical carbamoylation and cyanation of benzylic C(sp3)-H bonds.
  • Utilizing isocyanides as reaction partners.
  • Anodic oxidation of benzylic positions followed by isocyanide addition.
  • Mild reaction conditions, no external oxidant required.

Main Results:

  • Successful direct carbamoylation and cyanation of benzylic C(sp3)-H bonds.
  • Formation of α-aryl acetamide derivatives via nitrilium cation hydrolysis.
  • Formation of α-aryl acetonitrile derivatives via elimination of a tert-butyl cation.
  • Demonstration of a C-C bond formation under mild, electrochemical conditions.

Conclusions:

  • The developed electrochemical method offers a sustainable and efficient route to functionalize benzylic C(sp3)-H bonds.
  • This methodology provides access to important structural motifs present in numerous drugs and biologically relevant compounds.
  • The process avoids the need for prefunctionalized substrates and external oxidants, simplifying synthetic strategies.