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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Catalysis

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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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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Cross dehydrogenative C-O coupling catalysed by a catenane-coordinated copper(i).

Lihui Zhu1, Jiasheng Li1, Jun Yang1

  • 1Department of Chemistry, The University of Hong Kong Pokfulam Road Hong Kong P. R. China hoyuay@hku.hk.

Chemical Science
|June 7, 2021
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Summary

New copper(I) catalysts using mechanically interlocked catenane ligands enable efficient C(sp3)-O cross-coupling reactions. These dynamic catalysts offer improved performance and stability for organic synthesis.

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Area of Science:

  • Supramolecular Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Phenanthroline ligands are crucial in copper catalysis.
  • Mechanical bonds in catenanes offer unique structural properties.
  • Dehydrogenative cross-coupling reactions are important synthetic transformations.

Purpose of the Study:

  • To report copper(I) complexes supported by phenanthroline-containing catenane ligands.
  • To investigate their catalytic activity in C(sp3)-O dehydrogenative cross-coupling.
  • To demonstrate the advantages of catenane ligands in catalyst design.

Main Methods:

  • Synthesis of copper(I) complexes with catenane ligands.
  • Catalytic testing of C(sp3)-O dehydrogenative cross-coupling reactions.
  • Comparison with control complexes lacking mechanical interlocking.

Main Results:

  • The catenane-supported copper(I) catalyst is highly efficient and exhibits a broad substrate scope.
  • Transient exposure of the active copper site is enabled by the catenane structure.
  • The catalyst demonstrates stability and can be regenerated after substrate transformation.
  • Gram-scale transformations were achieved without significant loss of activity.

Conclusions:

  • Catenane ligands provide a dynamic and responsive copper coordination sphere.
  • The mechanical bond is a valuable design element for transition metal catalysts.
  • This approach offers advantages in efficiency and stability for catalytic applications.