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Related Concept Videos

¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

2.8K
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...
2.8K
Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

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

1.9K
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...
1.9K
Spin–Spin Coupling: Three-Bond Coupling (Vicinal Coupling)01:22

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

1.6K
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 involved orbitals. The...
1.6K
¹³C NMR: ¹H–¹³C Decoupling01:04

¹³C NMR: ¹H–¹³C Decoupling

2.0K
The probability of having two carbon-13 atoms next to each other is negligible because of the low natural abundance of carbon-13. Consequently, peak splitting due to carbon-carbon spin-spin coupling is not observed in spectra. However, protons up to three sigma bonds away split the carbon signal according to the n+1 rule, resulting in complicated spectra.
A broadband decoupling technique is used to simplify these complex, sometimes overlapping, signals. Broadband decoupling relies on a...
2.0K
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
C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

8.0K
The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.
8.0K

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Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology
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Stille coupling via C-N bond cleavage.

Dong-Yu Wang1,2, Masatoshi Kawahata3, Ze-Kun Yang1

  • 1Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo-to 113-0033, Japan.

Nature Communications
|October 1, 2016
PubMed
Summary

This study introduces a novel nickel-catalyzed Stille cross-coupling reaction that cleaves carbon-nitrogen bonds in quaternary ammonium salts. This method efficiently synthesizes biaryl compounds, expanding synthetic chemistry applications.

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cross-coupling reactions are essential for synthesizing functional molecules, with broad applications in phenols, anilines, alcohols, and amines.
  • Transforming amines and their derivatives often requires robust and versatile synthetic strategies.

Purpose of the Study:

  • To develop a novel nickel-catalyzed Stille cross-coupling reaction for quaternary ammonium salts.
  • To achieve C-N bond cleavage in quaternary ammonium salts for biaryl synthesis.

Main Methods:

  • Utilized nickel(0) bis(1,5-cyclooctadiene) (Ni(cod)2) as a catalyst with an imidazole ligand.
  • Employed cesium fluoride (CsF) as a promoter in the reaction between quaternary ammonium salts and arylstannanes.
  • Investigated reaction mechanisms through experimental studies, computational findings, and X-ray diffraction of nickel intermediates.

Main Results:

  • Successfully demonstrated the Ni-catalyzed Stille cross-coupling of quaternary ammonium salts via C-N bond cleavage.
  • Achieved the synthesis of biaryl compounds from aryl/alkyl-trimethylammonium salts and arylstannanes in a 1:1 molar ratio.
  • Showcased broad functional group compatibility in the resulting biaryl products.

Conclusions:

  • The developed Ni-catalyzed Stille cross-coupling offers a new pathway for transforming amines and quaternary ammonium salts.
  • This methodology provides a versatile route to multi-aromatic compounds with potential for wide applicability in organic synthesis.