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Related Concept Videos

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.9K
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.
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...
2.9K
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)

1.7K
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.
The extent of coupling depends on the C‑C bond length, the two H‑C‑C angles, any electron-withdrawing substituents, and the dihedral angle between the...
1.7K
C–C Bond Formation: Aldol Condensation Overview01:10

C–C Bond Formation: Aldol Condensation Overview

18.4K
Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
18.4K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.6K
Coupling interactions are strongest between NMR-active nuclei bonded to each other, where spin information can be transmitted directly through the pair of bonding electrons. While nuclei polarize their electrons to the opposite spins, the bonding electron pair has opposite spins. Configurations with antiparallel nuclear spins are expected to be lower in energy. When coupling makes antiparallel states more favorable, J is considered to have a positive value. The one-bond coupling constant, 1J,...
1.6K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

2.0K
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.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
2.0K
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

2.4K
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.
2.4K

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Cross-dehydrogenative coupling for the intermolecular C-O bond formation.

Igor B Krylov1, Vera A Vil'1, Alexander O Terent'ev1

  • 1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russia.

Beilstein Journal of Organic Chemistry
|February 12, 2015
PubMed
Summary

This review covers cross-dehydrogenative C-O coupling reactions, focusing on studies since 2000. It classifies methods by the carbon reagent (CH-reagent) and oxidative systems, highlighting C-H activation for C-O bond formation.

Keywords:
C–H functionalizationC–O bond formationacyloxylationalkoxylationcross-dehydrogenative couplingoxidative cross-coupling

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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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
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cross-dehydrogenative C-O coupling is a key transformation for forming carbon-oxygen bonds.
  • Recent advancements have expanded the scope and efficiency of these reactions.
  • Understanding the role of different reagents is crucial for reaction design.

Purpose of the Study:

  • To review primary publications on cross-dehydrogenative C-O coupling, emphasizing studies post-2000.
  • To classify reactions based on the nature of the carbon reagent (CH-reagent) and oxidative systems.
  • To discuss related C-H activation processes for intermolecular C-O bond formation.

Main Methods:

  • Literature review of primary publications.
  • Classification of reactions based on C-reagent structures and oxidative systems.
  • Analysis of various C-reagents (e.g., directing functional groups, activated C-H bonds) and O-reagents (e.g., alcohols, carboxylic acids).

Main Results:

  • The review categorizes cross-dehydrogenative C-O coupling reactions primarily by the structure of the C-reagent.
  • Common O-reagents include alcohols and carboxylic acids, while diverse C-reagents are utilized.
  • Related C-H activation processes, such as acyloxylation, are also discussed.

Conclusions:

  • The choice of C-reagent significantly dictates the principles of cross-dehydrogenative C-O coupling.
  • This review provides a structured overview of recent developments in C-O bond formation via C-H activation.
  • The findings aid in understanding and designing efficient synthetic routes for C-O coupled products.