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Related Concept Videos

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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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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Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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Crossed Aldol Reactions: Overview01:04

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Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

3.2K
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...
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PCET-mediated deconstructive cross-coupling of aliphatic alcohols.

Yeersen Patehebieke1, Rima Charaf2, Kumar Bhaskar Pal1

  • 1Department of Chemistry and Molecular Biology, University of Gothenburg Gothenburg SE 41390 Sweden carl.wallentin@chem.gu.se.

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A new catalytic system enables the deconstructive arylation of alcohols to form C(sp3)-C(sp2) bonds. This method efficiently generates alkyl radicals from alcohols for versatile cross-coupling reactions.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Photochemistry

Background:

  • Aliphatic alcohols are common feedstocks but challenging precursors for C-C bond formation.
  • Traditional methods often require harsh conditions or lack functional group tolerance.
  • Developing efficient arylation methods for alcohols is crucial for synthetic chemistry.

Purpose of the Study:

  • To develop a practical deconstructive arylation of aliphatic alcohols.
  • To establish a synergistic photoredox and nickel dual catalytic system for C(sp3)-C(sp2) bond formation.
  • To expand the scope of using alcohols as alkyl radical precursors.

Main Methods:

  • Utilizing a synergistic photoredox and nickel dual catalytic system.
  • Employing proton-coupled electron transfer (PCET) for radical generation via β-scission.
  • Optimization of reaction conditions for broad functional group tolerance and chemoselectivity.

Main Results:

  • Efficient formation of C(sp3)-C(sp2) bonds between alcohols and aryl halides.
  • Successful arylation of challenging tertiary alcohol substrates with good yields.
  • Confirmation of the PCET pathway for radical generation using transient absorption spectroscopy.

Conclusions:

  • The developed method offers a versatile approach for the deconstructive arylation of alcohols.
  • This strategy broadens the utility of alcohols in cross-coupling reactions.
  • The synergistic catalysis provides a powerful tool for constructing complex molecular architectures.