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Chalcogen-Bonding Catalysis with Telluronium Cations.

Robin Weiss1, Emmanuel Aubert2, Patrick Pale1

  • 1LASYROC, UMR 7177, University of Strasbourg, 1 Rue Blaise Pascal, 67000, Strasbourg, France.

Angewandte Chemie (International Ed. in English)
|June 24, 2021
PubMed
Summary
This summary is machine-generated.

Telluronium cations show remarkable catalytic activity in organic reactions, acting as potent Lewis acids. This study highlights their potential as novel organocatalysts, leveraging chalcogen bonding interactions.

Keywords:
Lewis acidschalcogen bondingnon-covalent interactionsorganocatalysistellurium

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Supramolecular Chemistry

Background:

  • Chalcogen bonding involves interactions between electrodeficient chalcogen atoms and Lewis bases.
  • Tellurium is a strong Lewis acid, yet Te-based compounds are underutilized in organocatalysis.
  • Organocatalysis offers sustainable and efficient synthetic routes in chemistry.

Purpose of the Study:

  • To investigate the catalytic potential of telluronium cations in organic synthesis.
  • To demonstrate the application of telluronium cations in benchmark reactions.
  • To elucidate the mechanism of catalysis involving chalcogen bonding.

Main Methods:

  • Catalysis of Friedel-Crafts bromination, bromolactonization, and aza-Diels-Alder reactions.
  • Utilized low catalyst loadings for efficiency.
  • Employed multi-nuclear NMR spectroscopy (17O, 31P, 125Te) and Density Functional Theory (DFT) calculations.

Main Results:

  • Telluronium cations exhibited significant catalytic activity in the tested reactions.
  • Effective catalysis was achieved at low catalyst concentrations.
  • Chalcogen bonding interactions between telluronium cations and Lewis bases were confirmed.

Conclusions:

  • Telluronium cations are effective organocatalysts for key organic transformations.
  • Chalcogen bonding is the key interaction facilitating telluronium-catalyzed reactions.
  • This work opens new avenues for developing Te-based organocatalysts.