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Related Concept Videos

Catalysis02:50

Catalysis

29.8K
The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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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 involved orbitals. The...
1.3K
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
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

2.1K
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.
2.1K
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...
2.4K
Spin–Spin Coupling: One-Bond Coupling01:17

Spin–Spin Coupling: One-Bond Coupling

1.3K
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,...
1.3K

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Related Experiment Video

Updated: Dec 14, 2025

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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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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General Cu-Catalyzed Csp-S Coupling.

Éric Godin1, Jeffrey Santandrea1, Antoine Caron1

  • 1Département de Chimie, Centre for Green Chemistry and Catalysis, Université de Montréal, Complexe des Sciences, 1375 Avenue Thérèse-Lavoie-Roux, Montréal, Québec H2V 0B3, Canada.

Organic Letters
|July 16, 2020
PubMed
Summary
This summary is machine-generated.

This study introduces a copper-catalyzed reaction for efficiently coupling thiols with bromoalkynes. This novel method provides a mild and selective route to synthesize diverse sulfur-containing alkynes.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Efficient synthesis of carbon-heteroatom bonds is crucial in organic chemistry.
  • Alkynes are versatile building blocks, but their functionalization can be challenging.
  • Developing mild and selective coupling reactions is an ongoing area of research.

Purpose of the Study:

  • To develop a novel copper-catalyzed method for Csp-S bond formation.
  • To enable the synthesis of diverse sulfur-containing alkynes using thiols and bromoalkynes.
  • To explore the preparation of challenging bis-heteroatom-functionalized alkynes.

Main Methods:

  • Copper-catalyzed cross-coupling reaction.
  • Utilized thiols (aryl, alkyl, silyl) and bromoalkynes as coupling partners.
  • Optimized reaction conditions for mildness, rapidity, and selectivity.

Main Results:

  • Achieved a mild, rapid, and selective Csp-S coupling reaction.
  • Demonstrated broad scope with 38 examples, yielding 50-99% product.
  • Successfully synthesized difficult-to-access bis-heteroatom-functionalized alkynes (S,S-, S,P-, S,N-).

Conclusions:

  • The developed copper-catalyzed method is highly effective for Csp-S coupling.
  • This approach offers a versatile and efficient route to various sulfur-containing alkynes.
  • The methodology expands synthetic possibilities for complex heteroatom-functionalized alkynes.