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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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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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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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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[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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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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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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Progress in copper-catalysed/mediated intramolecular dehydrogenative coupling.

Rasmi P Bhaskaran1, Kalinga H Nayak1, Mariswamy K Sreelekha1

  • 1Department of Chemistry National Institute of Technology Karnataka Surathkal, Mangalore, India - 575025. pbbeneesh@nitk.edu.in.

Organic & Biomolecular Chemistry
|November 30, 2022
PubMed
Summary
This summary is machine-generated.

Copper catalysts offer a green, cost-effective alternative for C-H functionalization. This review details copper-mediated intramolecular dehydrogenative coupling for efficient synthesis of complex molecular structures.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Transition metal-catalyzed C-H functionalization is key for bond formation.
  • Early methods relied on expensive metals; focus shifted to earth-abundant metals like copper.
  • Copper catalysis presents a cost-effective, less toxic, and greener alternative.

Purpose of the Study:

  • To comprehensively review copper-mediated intramolecular dehydrogenative coupling reactions.
  • To highlight the synthesis of carbon-carbon and carbon-heteroatom bonds.
  • To focus on copper's role in regioselective C-H activation.

Main Methods:

  • Review of literature on copper-catalyzed intramolecular dehydrogenative coupling.
  • Analysis of reactions involving C-H and heteroatom-H bond activation.
  • Emphasis on reactions utilizing oxygen as the terminal oxidant.

Main Results:

  • Copper catalysts enable regioselective activation of inert C-H bonds.
  • Intramolecular dehydrogenative coupling efficiently produces complex polycyclic scaffolds.
  • Oxygen is frequently employed as the terminal oxidant in these copper-catalyzed reactions.

Conclusions:

  • Copper-based intramolecular dehydrogenative coupling is a powerful synthetic strategy.
  • This approach offers a sustainable and efficient route to valuable molecular architectures.
  • This review provides the first comprehensive account of copper-based intramolecular dehydrogenative coupling.