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Related Concept Videos

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

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

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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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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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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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Thermal Electrocyclic Reactions: Stereochemistry01:17

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

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Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
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Electroinduced Reductive and Dearomative Alkene-Aldehyde Coupling.

Liam J Franov1, Tayla L Wilsdon1, Milena L Czyz1

  • 1School of Chemistry, The University of Melbourne, Parkville, Victoria 3010, Australia.

Journal of the American Chemical Society
|October 17, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a novel electrochemical method for coupling alkenes and heteroarenes with aldehydes, creating diverse C(sp3)-hybridized alcohols. This catalyst-free approach overcomes limitations of current methods for synthesizing complex oxygenated scaffolds.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • Direct coupling of alkenes and aldehydes is challenging due to limitations in substrate tolerance and functional group compatibility.
  • Existing methods for C-C π-bond coupling with aldehydes are often restricted in complex molecular settings.

Purpose of the Study:

  • To develop an efficient and versatile method for the direct coupling of simple alkenes, heteroarenes, and unactivated aliphatic aldehydes.
  • To enable the synthesis of diverse C(sp3)-hybridized alcohols from readily available feedstocks.

Main Methods:

  • Utilized electrochemically induced reductive activation of C-C π-bonds via rapid alternating polarity (rAP) electrolysis.
  • Employed catalyst-free conditions for the reductive coupling process.
  • Investigated the generation and reactivity of radical anion intermediates.

Main Results:

  • Achieved direct coupling of alkenes and heteroarenes with aliphatic aldehydes, yielding diverse C(sp3)-hybridized alcohols.
  • Demonstrated chemoselective generation of olefinic radical anion intermediates using rAP electrolysis.
  • Reported unprecedented reductive dearomative functionalization for heterocyclic compounds.

Conclusions:

  • The developed rAP electrolysis protocol provides a versatile and efficient route to C(sp3)-rich oxygenated scaffolds.
  • This catalyst-free method expands the scope of reductive coupling reactions for organic synthesis.
  • Offers straightforward access to structurally diverse alcohol products from simple feedstocks.