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¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.4K
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...
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Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

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

1.3K
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...
1.3K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.2K
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,...
1.2K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

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

1.5K
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...
1.5K
Ligand Binding and Linkage00:49

Ligand Binding and Linkage

4.4K
Allosteric proteins have more than one ligand binding site; the binding of a ligand to any of these sites influences the binding of ligands to the other sites. When a protein is allosteric, its binding sites are called coupled or linked.  In the case of enzymes, the site that binds to the substrate is known as the active site and the other site is known as the regulatory site. When a ligand binds to the regulatory site, this leads to conformational changes in the protein that can influence...
4.4K
Ligand Binding and Linkage00:49

Ligand Binding and Linkage

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Ligand-Enabled Pd-Catalyzed C(sp3)-H/C(sp2)-H Coupling.

Haiwei Zhao1, Zhen Li1, Xinyu Zhu1

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Journal of the American Chemical Society
|May 4, 2026
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Summary
This summary is machine-generated.

Researchers developed new pyridone-morpholine ligands for palladium-catalyzed C-H arylation of carboxylic acids with simple arenes. This method enables efficient coupling of aliphatic C-H bonds with diverse (hetero)aromatic compounds, expanding synthetic possibilities.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Palladium-catalyzed C-H arylation of carboxylic acids is well-established using aryl boron and aryl iodide reagents.
  • Arylation using simple arenes as coupling partners remains a significant synthetic challenge.
  • Development of novel ligands is crucial for expanding the scope of C-H functionalization reactions.

Purpose of the Study:

  • To develop a novel catalytic system for the direct arylation of free carboxylic acids with simple arenes.
  • To enable the C-H functionalization of both acyclic and cycloalkane carboxylic acids.
  • To expand the utility of palladium catalysis in C-H bond activation with arenes.

Main Methods:

  • Development of novel pyridone-morpholine ligands for palladium catalysis.
  • Investigation of β-methylene C-H (hetero)arylation of acyclic aliphatic acids.
  • Exploration of γ-(hetero)arylation of cycloalkane carboxylic acids using benzene, furan, thiophene, and pyridine.
  • Mechanistic studies including ligand-promoted dehydrogenation and C(sp2)-H activation.
  • Construction of a dual-ligand catalysis system for C(sp3)-H bond coupling with indoles and pyrroles.

Main Results:

  • Successful β-methylene C-H (hetero)arylation of acyclic aliphatic acids with arenes.
  • Efficient γ-(hetero)arylation of cycloalkane carboxylic acids using benzene, furan, thiophene, and pyridine.
  • Demonstration of a dual-ligand system enabling coupling with indoles and pyrroles.
  • Mechanistic insights suggest a pathway involving ligand-promoted dehydrogenation and C(sp2)-H activation.

Conclusions:

  • Novel pyridone-morpholine ligands facilitate palladium-catalyzed C-H arylation of carboxylic acids with simple arenes.
  • The developed methodology allows for the efficient functionalization of aliphatic C-H bonds.
  • Mechanistic understanding guided the development of a dual-ligand system for broader substrate scope.