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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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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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Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

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The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
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Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation00:43

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

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As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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1.9K
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.
1.9K

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Copper-catalyzed deacetonative Sonogashira coupling.

Yury N Kotovshchikov1, Artem A Binyakovsky1, Gennadij V Latyshev1

  • 1Chemistry Department, M. V. Lomonosov Moscow State University, Leninskiye Gory 1/3, Moscow 119991, Russia. kotovshchikov@org.chem.msu.ru.

Organic & Biomolecular Chemistry
|September 22, 2022
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Summary

A new, cost-effective method synthesizes internal alkynes using tertiary propargyl alcohols and aryl halides. This palladium- and phosphine-free process simplifies alkyne synthesis and shows broad applicability, including with steroidal compounds.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Tertiary propargyl alcohols are versatile precursors for alkyne synthesis.
  • Palladium (Pd)- and phosphine-based catalysts are commonly used but can be expensive and toxic.
  • Developing efficient, cost-effective, and environmentally benign synthetic routes is crucial in organic chemistry.

Purpose of the Study:

  • To develop a novel, convenient, and cost-effective protocol for synthesizing internal alkynes.
  • To establish a palladium- and phosphine-free method for C(sp)-C(sp2) cross-coupling reactions.
  • To demonstrate the broad applicability and synthetic utility of the developed method.

Main Methods:

  • A tandem reaction sequence involving base-promoted retro-Favorskii fragmentation followed by copper (Cu)-catalyzed C(sp)-C(sp2) cross-coupling.
  • Utilizing readily available and inexpensive reagents, including catalysts, additives, bases, and solvents.
  • Testing the functional group tolerance of the developed synthetic protocol.

Main Results:

  • Successful assembly of internal alkynes from tertiary propargyl alcohols and (het)aryl halides.
  • The protocol is palladium- and phosphine-free, enhancing its practicality and cost-effectiveness.
  • Demonstrated good functional group tolerance and synthetic utility through the alkynylation of vinyl iodides from natural steroidal hormones.

Conclusions:

  • The developed tandem approach offers a convenient and economical route to internal alkynes.
  • The absence of palladium and phosphine ligands makes the method environmentally friendlier and more accessible.
  • The method's applicability to complex molecules like steroidal compounds highlights its synthetic value.