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Related Concept Videos

Coupled Reactions01:17

Coupled Reactions

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Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions. 
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Crossed Aldol Reactions: Overview01:04

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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.
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Crossed Aldol Reaction Using Weak Bases01:14

Crossed Aldol Reaction Using Weak Bases

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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.
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Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

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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.
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Crossing Over01:34

Crossing Over

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Unlike mitosis, meiosis aims for genetic diversity in its creation of haploid gametes. Dividing germ cells first begin this process in prophase I, where each chromosome—replicated in S phase—is now composed of two sister chromatids (identical copies) joined centrally.
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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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Upgrading Cross-Coupling Reactions for Biaryl Syntheses.

Yun-Fei Zhang1,2, Zhang-Jie Shi1,3,4

  • 1Department of Chemistry , Fudan University , Shanghai 200433 , China.

Accounts of Chemical Research
|October 31, 2018
PubMed
Summary
This summary is machine-generated.

This study explores innovative cross-coupling reactions to synthesize biaryl compounds more efficiently. Researchers developed strategies using readily available arenes and earth-abundant catalysts, reducing costs and environmental impact.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Transition-metal catalyzed cross-coupling reactions are vital for biaryl synthesis.
  • Current methods often rely on aryl halides and organometallic reagents, which require tedious preparation.
  • Developing alternative, cost-effective, and sustainable methods is highly desirable.

Purpose of the Study:

  • To develop novel cross-coupling strategies for biaryl construction.
  • To replace traditional coupling partners with readily available surrogates like arenes.
  • To explore catalysis using earth-abundant metals and transition-metal-free systems.

Main Methods:

  • Investigated C-O activation using arenol-based electrophiles, aryl carboxylates, and arenols.
  • Examined oxidative cross-coupling reactions based on C-H activation with aryl metallic reagents.
  • Improved arene-organohalide cross-coupling using earth-abundant metals (Fe, Co) and transition-metal-free systems.
  • Developed strategies for direct cross-dehydrogenative arylation between two different arenes, addressing selectivity challenges.

Main Results:

  • Successfully applied C-O activation methodologies with extended coupling partners.
  • Adapted catalytic systems for effective C-H activation cross-coupling with various organometallic reagents.
  • Demonstrated improved cross-coupling using earth-abundant and transition-metal-free catalysts.
  • Achieved selective C-H activation and cross-coupling between two different arenes through tailored strategies.

Conclusions:

  • Developed four distinct strategies to enhance cross-coupling reactions for biaryl synthesis.
  • Showcased the potential of using inexpensive and abundant starting materials like arenes.
  • Highlighted the advancement of catalytic systems, including earth-abundant and metal-free options.
  • Aimed to inspire further research in C-C bond formation using sustainable chemical feedstocks.