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Related Concept Videos

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

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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¹H NMR: Long-Range Coupling01:27

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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

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Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Cobalt-catalyzed intermolecular C(sp(2))-O cross-coupling.

Debasish Kundu1, Manisha Tripathy2, Pintu Maity1

  • 1Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata-700032 (India).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 1, 2015
PubMed
Summary
This summary is machine-generated.

A novel cobalt and copper dual catalyst system enables ligand-free C-O cross-coupling reactions. This efficient method synthesizes various aryl and heteroaryl ethers from alcohols and halides.

Keywords:
CO couplingcobaltcopperethershomogeneous catalysis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • C-O cross-coupling reactions are crucial for synthesizing ethers.
  • Developing efficient and ligand-free catalytic systems remains a challenge.

Purpose of the Study:

  • To develop a novel Cobalt/Copper dual catalyst system for C(sp2)-O cross-coupling.
  • To achieve ligand-free coupling of aryl/heteroaryl alcohols with vinyl/aryl halides.

Main Methods:

  • Utilizing a Cobalt(II) catalyst in conjunction with Copper(I).
  • Performing the cross-coupling reaction under ligand-free conditions.
  • Investigating the role of copper in the transmetalation step.

Main Results:

  • Successful C(sp2)-O cross-coupling between aryl/heteroaryl alcohols and vinyl/aryl halides.
  • Copper(I) was found to play a significant role in transmetalation.
  • The Co/Cu dual catalyst system facilitated the synthesis of diverse aryl-vinyl, heteroaryl-styryl, aryl-aryl, and heteroaryl-heteroaryl ethers.
  • The reaction proceeded efficiently without the need for any ligand or additive.

Conclusions:

  • A novel and efficient Cobalt/Copper dual catalyst system for C-O cross-coupling has been established.
  • The developed method offers a straightforward approach to synthesize various diaryl and aryl-vinyl ethers.
  • The absence of ligands and additives simplifies the reaction procedure and broadens its applicability.