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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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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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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...
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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
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Catalytic C-CN bond activation.

Yoshiaki Nakao1

  • 1Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto, 615-8510, Japan, nakao.yoshiaki.8n@kyoto-u.ac.jp.

Topics in Current Chemistry
|February 20, 2014
PubMed
Summary
This summary is machine-generated.

Transition metal catalysis enables synthetic organic reactions via C-CN bond activation. This review covers key pathways and their applications in nitrile functionalization and cyanation reactions.

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Area of Science:

  • Synthetic organic chemistry
  • Organometallic chemistry
  • Catalysis

Background:

  • The activation of carbon-nitrogen triple bonds (C-CN) is crucial for organic synthesis.
  • Transition metal catalysis offers powerful methods for C-CN bond activation.

Purpose of the Study:

  • To review synthetic organic reactions facilitated by C-CN bond activation using transition metal catalysis.
  • To elucidate the primary mechanisms of C-CN bond activation by metal complexes.

Main Methods:

  • Review of literature on transition metal-catalyzed C-CN bond activation.
  • Analysis of reaction pathways including oxidative addition and C-CN cleavage.
  • Examination of catalytic applications.

Main Results:

  • C-CN bond activation by metal complexes primarily occurs via oxidative addition or C-CN cleavage with silylisonitrile formation.
  • These elemental reactions have been successfully applied in various catalytic transformations.
  • Applications include hydrodecyanation, cross-coupling, cyanation, and carbocyanation reactions.

Conclusions:

  • Transition metal-catalyzed C-CN activation provides versatile synthetic routes.
  • The discussed pathways are effective for diverse nitrile functionalizations.
  • This methodology expands the utility of nitriles in organic synthesis.