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Related Concept Videos

Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

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.
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

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.
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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.
Crossed Aldol Reaction Using Weak Bases01:14

Crossed Aldol Reaction Using Weak Bases

This lesson deals with the crossed aldol reaction using weak bases. The self-condensation of an aldehyde having α hydrogen is prevented by adding it slowly to a mixture of formaldehyde and weak bases like hydroxide and alkoxide. Upon slow addition of the aldehyde, the base deprotonates the α carbon of the aldehyde to form the corresponding enolate. The enolate subsequently attacks the formaldehyde to form a single crossed product. Figure 1 depicts the aforementioned reaction.
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.
β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

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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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Cobalt-catalyzed cross-coupling reactions.

Corinne Gosmini1, Jeanne-Marie Bégouin, Aurélien Moncomble

  • 1Laboratoire Hétéroéléments et Coordination, Ecole Polytechnique, CNRS, 91128, Palaiseau Cedex, France. corinne.gosmini@polytechnique.edu

Chemical Communications (Cambridge, England)
|July 16, 2008
PubMed
Summary

Economical cobalt salts are effective replacements for expensive catalysts in cross-coupling reactions. This research details cobalt-catalyzed methods for synthesizing diverse functionalized compounds, tolerating various organic substrates and sensitive functional groups.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Expensive and toxic catalysts are traditionally used for cross-coupling reactions.
  • Cobalt salts offer an economical and less toxic alternative.

Purpose of the Study:

  • To demonstrate the utility of cobalt salts as catalysts in cross-coupling reactions.
  • To expand the scope of functionalized compounds synthesized via cobalt catalysis.

Main Methods:

  • Utilizing economical cobalt salts for catalytic cross-coupling.
  • Employing various organic compounds (RX) including alkyl, alkynyl, aryl, and allyl groups.
  • Accommodating halides (F, Cl, Br, I) and triflates as leaving groups.

Main Results:

  • Successfully extended the range of functionalized compounds achievable through cross-coupling.
  • Demonstrated tolerance of sensitive functional groups in cobalt-catalyzed reactions.
  • Developed methods for preparing functionalized compounds from organometallic species and direct cross-coupling.

Conclusions:

  • Cobalt-catalyzed cross-coupling reactions provide a versatile and efficient route to diverse functionalized organic compounds.
  • This approach offers a sustainable and cost-effective alternative to traditional methods.