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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
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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Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

6.6K
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.
6.6K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
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.
2.4K
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

2.3K
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.
2.3K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.9K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.9K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.2K
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.
5.2K

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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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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Copper-catalysed cross-coupling: an untapped potential.

Surendra Thapa1, Bijay Shrestha, Santosh K Gurung

  • 1Department of Chemistry & Chemical Biology, The University of New Mexico, Albuquerque, NM 87131, USA. rgiri@unm.edu.

Organic & Biomolecular Chemistry
|April 2, 2015
PubMed
Summary

Copper catalysts are versatile for creating carbon-carbon bonds through cross-coupling reactions. They efficiently join various organometallic reagents with halides, even enabling ligandless couplings.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organometallic Chemistry

Background:

  • Copper is an increasingly important catalyst for forming carbon-carbon bonds.
  • Cross-coupling reactions are essential for synthesizing complex organic molecules.

Purpose of the Study:

  • To review the advancements in copper-catalyzed cross-coupling reactions.
  • To highlight the versatility of copper catalysts in forming carbon-carbon bonds.

Main Methods:

  • Review of literature on copper-catalyzed cross-coupling reactions.
  • Analysis of copper's catalytic activity with various organometallic reagents (organomagnesium, organoboron, organosilicon, organoindium, organomanganese) and organic halides (alkyl, aryl, heteroaryl).

Main Results:

  • Copper catalysts demonstrate high efficacy in cross-coupling reactions with diverse organometallic reagents and halides.
  • Copper catalysts enable unique ligandless cross-coupling for aryl-heteroaryl and heteroaryl-heteroaryl bond formation.
  • Copper catalysis offers an alternative to palladium catalysis, often avoiding the need for specialized ligands.

Conclusions:

  • Copper is a versatile and effective catalyst for constructing carbon-carbon bonds via cross-coupling.
  • Copper-catalyzed reactions present advantages, including the potential for ligandless transformations.
  • Further advancements in copper catalysis are expected to expand its utility in organic synthesis.