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Related Concept Videos

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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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.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

4.3K
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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
21.8K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

4.7K
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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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Catalytic reversible alkene-nitrile interconversion through controllable transfer hydrocyanation.

Xianjie Fang1, Peng Yu1, Bill Morandi2

  • 1Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Nordrhein-Westfalen 45470, Germany.

Science (New York, N.Y.)
|February 26, 2016
PubMed
Summary

Researchers developed a nickel-catalyzed reaction for safer hydrocyanation of alkenes using nitriles. This method avoids toxic hydrogen cyanide (HCN) and offers new synthetic pathways for valuable chemicals.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Nitriles and alkenes are crucial building blocks in synthesizing materials, pharmaceuticals, and agrochemicals.
  • Traditional hydrocyanation methods often rely on toxic hydrogen cyanide (HCN), posing significant safety risks.
  • Developing safer and more versatile synthetic routes is essential for modern chemical research.

Purpose of the Study:

  • To report a novel nickel-catalyzed transfer hydrocyanation reaction between alkyl nitriles and alkenes.
  • To provide a safer alternative to traditional HCN-based hydrocyanation methods.
  • To explore new synthetic possibilities, including retro-hydrocyanation and anti-Markovnikov regioselectivity.

Main Methods:

  • Utilized a nickel catalyst to mediate the transfer hydrocyanation reaction.
  • Employed a wide range of alkyl nitriles and alkenes (60 examples) to demonstrate substrate scope.
  • Investigated thermodynamically controlled transfer reactions for reversible alkene hydrofunctionalization.

Main Results:

  • Successfully demonstrated a nickel-catalyzed transfer hydrocyanation of diverse alkyl nitriles and alkenes.
  • Achieved anti-Markovnikov regioselectivity in the hydrocyanation process.
  • Showcased the potential for reversible hydrofunctionalization, circumventing hazardous reagents.

Conclusions:

  • The developed nickel-catalyzed transfer hydrocyanation offers a safer and efficient alternative to traditional methods.
  • This strategy expands the synthetic utility of nitriles and alkenes in organic synthesis.
  • The work presents a significant advancement in developing sustainable and controlled hydrofunctionalization reactions.