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Related Concept Videos

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

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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.
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids01:24

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Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
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Preparation of Alkynes: Alkylation Reaction02:27

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Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Updated: Jun 14, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Reductive alkyl-alkyl coupling from isolable nickel-alkyl complexes.

Samir Al Zubaydi1, Shivam Waske1, Volkan Akyildiz1,2

  • 1Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.

Nature
|August 29, 2024
PubMed
Summary

This study introduces a versatile method for combining two alkyl groups using nickel catalysis, overcoming limitations in traditional organic synthesis. This approach allows for the flexible construction of complex molecules from common building blocks like amines, acids, and halides.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry
  • Synthetic Chemistry

Background:

  • Selective cross-coupling of alkyl electrophiles is crucial for complex molecule synthesis but faces limitations with common building blocks.
  • Existing methods are often substrate-specific, restricting the exploration of chemical space.
  • There is a need for a general strategy enabling combinatorial approaches to alkyl-alkyl cross-coupling.

Purpose of the Study:

  • To develop a general and combinatorial method for alkyl-alkyl cross-coupling reactions.
  • To overcome the limitations of substrate specificity in current synthetic methodologies.
  • To enable the diversification of various organic molecules using a unified approach.

Main Methods:

  • Discovery of persistent nickel(alkyl) complexes formed via oxidative addition of alkyl halides, redox-active esters, or pyridinium salts.
  • Isolation or direct telescoping of these nickel(alkyl) intermediates for coupling with a second alkyl electrophile.
  • Application of crystallographic analysis, stereochemical probes, and spectroscopic studies to understand the organometallic chemistry.

Main Results:

  • A general solution for combinatorial alkyl-alkyl cross-coupling reactions has been achieved.
  • Unusually persistent Ni(alkyl) complexes were identified, enabling cross-selective couplings previously unknown.
  • The methodology demonstrated rapid diversification of amino acids, natural products, pharmaceuticals, and drug-like building blocks through dehalogenative, decarboxylative, or deaminative coupling.

Conclusions:

  • This work presents a significant advancement in organic synthesis, offering a versatile platform for constructing complex molecules.
  • The developed methodology broadens the scope of accessible alkyl substrates and facilitates combinatorial library synthesis.
  • Insights into the organometallic chemistry of Ni(alkyl) complexes provide a foundation for further synthetic innovations.