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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...
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation01:22

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is activated by...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Published on: February 16, 2020

Catalytic (asymmetric) methylene transfer to aldehydes.

Alessandro Piccinini1, Sarah A Kavanagh, Paul B Connon

  • 1Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.

Organic Letters
|January 9, 2010
PubMed
Summary

Sulfide catalysts show poor activity in methylene transfer reactions due to inefficient ylide formation. Using methyl triflate with cyclic thiolanes enables efficient catalytic aldehyde epoxidation at low catalyst loadings.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Sulfides are often poor catalysts for sulfonium-ylide-mediated methylene transfer to aldehydes.
  • The key limitation in catalytic cycles involving sulfides is the inefficient formation of the active ylide intermediate.
  • Traditional electrophilic alkylation methods fail to provide sufficient efficiency for catalytic sulfide use.

Purpose of the Study:

  • To investigate the reasons behind the poor catalytic activity of sulfides in methylene transfer reactions.
  • To identify an effective method for generating sulfonium ylides catalytically for aldehyde epoxidation.

Main Methods:

  • Investigated the catalytic cycle of sulfide-mediated methylene transfer to aldehydes.
  • Explored the alkylation of cyclic thiolanes using various electrophiles.
  • Evaluated the efficiency of aldehyde epoxidation using optimized sulfide catalysts and phosphazene bases.

Main Results:

  • Ylide formation was identified as the rate-limiting and problematic step in the catalytic cycle.
  • Methyl triflate was found to rapidly alkylate cyclic thiolanes under mild conditions.
  • The optimized system demonstrated efficient aldehyde epoxidation using cyclic thiolanes at loadings as low as 10 mol %.

Conclusions:

  • The catalytic activity of sulfides in methylene transfer is hindered by inefficient ylide formation.
  • Methyl triflate activation of cyclic thiolanes provides a viable route for efficient sulfonium ylide generation.
  • This methodology enables effective catalytic aldehyde epoxidation with low catalyst loadings.