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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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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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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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Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
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The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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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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A Ball-Milling-Enabled Cross-Electrophile Coupling.

Andrew C Jones1, William I Nicholson1, Jamie A Leitch2

  • 1Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, United Kingdom.

Organic Letters
|August 3, 2021
PubMed
Summary
This summary is machine-generated.

This study introduces nickel-catalyzed cross-electrophile coupling using ball-milling, avoiding solvents and sensitive setups. This mechanochemical method efficiently forms C-C bonds, yielding 28 products.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Mechanochemistry

Background:

  • Cross-electrophile coupling reactions are vital for C-C bond formation.
  • Traditional methods often require inert atmospheres and bulk solvents.

Purpose of the Study:

  • To develop a solvent-free, air-stable method for nickel-catalyzed cross-electrophile coupling.
  • To utilize ball-milling for efficient mechanochemical synthesis.

Main Methods:

  • Nickel-catalyzed coupling of aryl halides and alkyl halides.
  • Employing ball-milling as the mechanochemical activation method.
  • Utilizing various zinc sources to facilitate the nickel catalytic cycle.

Main Results:

  • Successful reductive C-C bond formation under solvent-free conditions.
  • Achieved reaction completion within 2-hour timeframes.
  • Synthesized 28 diverse cross-electrophile coupled products.

Conclusions:

  • Ball-milling provides an effective platform for nickel-catalyzed cross-electrophile coupling.
  • This mechanochemical approach offers a sustainable and efficient alternative to traditional methods.
  • The methodology is robust and versatile for synthesizing various coupled products.