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Related Concept Videos

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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 surface of...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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 mixture.

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Silver-catalyzed silicon-hydrogen bond functionalization by carbene insertion.

M José Iglesias1, M Carmen Nicasio, Ana Caballero

  • 1Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencia de los Materiales, Unidad Asociada al CSIC, Centro de Investigación en Química Sostenible, Universidad de Huelva, Campus de El Carmen, 21007-Huelva, Spain.

Dalton Transactions (Cambridge, England : 2003)
|November 2, 2012
PubMed
Summary

This study introduces a novel silver catalyst for the functionalization of silicon-hydrogen bonds using ethyl diazoacetate (EDA). The catalyst

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Silicon Chemistry

Background:

  • Silicon-hydrogen (Si-H) bond functionalization is crucial in synthetic chemistry.
  • Carbene insertion reactions offer a pathway for C-Si bond formation.
  • Developing new catalytic systems for these transformations is an ongoing challenge.

Purpose of the Study:

  • To report the first catalytic system using a silver-based catalyst for Si-H bond functionalization via carbene insertion.
  • To investigate the influence of silane substituents on reactivity.
  • To explore the scope of diazo compounds in this reaction.

Main Methods:

  • Utilized a silver-based catalyst for the reaction between substituted silanes and ethyl diazoacetate (EDA).
  • Performed competition experiments with various substituted silanes to determine relative reactivity.
  • Screened different diazo compounds to assess their efficacy.

Main Results:

  • Successfully demonstrated silver-catalyzed insertion of ethyl carbene (:CHCO(2)Et) into Si-H bonds.
  • Established that silane reactivity is influenced by Si-H bond dissociation energy, with tertiary silanes being most reactive for ethyl-substituted silanes.
  • Observed a reversed reactivity order (secondary > primary ≈ tertiary) for phenyl-substituted silanes due to steric effects.
  • Identified N(2)C(Ph)CO(2)Et as a viable alternative diazo compound, while other N(2)C(R)CO(2)Et derivatives showed lower conversions.

Conclusions:

  • Silver catalysts can effectively mediate the insertion of carbenes into Si-H bonds.
  • Steric and electronic factors of both silanes and diazo compounds play a significant role in catalytic activity and selectivity.
  • This work expands the catalytic toolbox for silicon functionalization.