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Related Concept Videos

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

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The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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

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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: Asymmetric Catalytic Hydrogenation02:17

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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.
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First Base-Free Catalytic Wittig Reaction.

Marie-Luis Schirmer1, Sven Adomeit1, Thomas Werner1

  • 1Leibniz-Institut für Katalyse e.V., Albert-Einstein-Strasse 29a, 18059 Rostock, Germany.

Organic Letters
|May 29, 2015
PubMed
Summary

This study introduces the first base-free catalytic Wittig reaction using tributylphosphine (Bu3P) as an organocatalyst. This novel method efficiently converts maleates and fumarates with various aldehydes, yielding products with high selectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The Wittig reaction is a fundamental tool in organic synthesis for forming carbon-carbon double bonds.
  • Traditional Wittig reactions often require strong bases, limiting substrate scope and functional group tolerance.
  • Development of base-free catalytic methods is highly desirable for milder and more efficient synthesis.

Purpose of the Study:

  • To report the first base-free catalytic Wittig reaction.
  • To utilize readily available tributylphosphine (Bu3P) as an organocatalyst.
  • To explore the scope and limitations of this new synthetic approach.

Main Methods:

  • Employing tributylphosphine (Bu3P) as an organocatalyst (5 mol %).
  • Utilizing Michael addition of phosphine to acceptor-substituted alkenes to form ylides.
  • Reacting ylides with various aldehydes (aromatic, heteroaromatic, aliphatic).
  • Characterization using (1)H NMR spectroscopy to confirm reaction intermediates.

Main Results:

  • Successful base-free catalytic Wittig reaction achieved.
  • Various maleates and fumarates reacted with diverse aldehydes.
  • High isolated yields (up to 95%) and excellent E/Z-selectivities (up to 99:1) were obtained.
  • Stereoconvergent reaction pathway observed for maleates and fumarates.

Conclusions:

  • A novel and efficient base-free catalytic Wittig reaction has been developed.
  • Tributylphosphine serves as an effective organocatalyst for this transformation.
  • The reaction offers broad scope and high stereoselectivity, making it valuable for organic synthesis.