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Chalcogen⋅⋅⋅π Bonding Catalysis.

Xiangjin Kong1, Pan-Pan Zhou2, Yao Wang1

  • 1School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, Jinan, 250100, China.

Angewandte Chemie (International Ed. in English)
|February 2, 2021
PubMed
Summary
This summary is machine-generated.

This study introduces chalcogen⋅⋅⋅π bonding catalysis, using sulfur and selenium interactions to activate π systems for chemical reactions. These noncovalent forces efficiently drive Diels-Alder cycloadditions, with double selenium interactions controlling stereoselectivity.

Keywords:
catalysischalcogen bondingchalcogen⋅⋅⋅π interactioncycloadditionnoncovalent interaction

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Area of Science:

  • Chemical catalysis
  • Supramolecular chemistry
  • Organic synthesis

Background:

  • Sulfur⋅⋅⋅π bonding is prevalent in biological systems but underexplored in chemical processes.
  • Noncovalent interactions offer unique opportunities for controlling chemical reactivity and selectivity.

Purpose of the Study:

  • To introduce and demonstrate the concept of chalcogen⋅⋅⋅π bonding catalysis.
  • To explore the activation of π systems via chalcogen⋅⋅⋅π interactions.
  • To investigate the application of this catalysis in cycloaddition reactions.

Main Methods:

  • Proof-of-concept studies using a vinylindole-based Diels-Alder reaction.
  • Investigation of sulfur (S)⋅⋅⋅π and selenium (Se)⋅⋅⋅π bonding interactions.
  • Analysis of reaction efficiency and stereoselectivity.

Main Results:

  • Chalcogen⋅⋅⋅π bonding interactions (S⋅⋅⋅π and Se⋅⋅⋅π) efficiently drive Diels-Alder cycloaddition reactions.
  • A simultaneously double Se⋅⋅⋅π bonding interaction was observed to direct stereoselectivity.
  • Demonstrated the potential of chalcogen⋅⋅⋅π interactions as a catalytic tool.

Conclusions:

  • Chalcogen⋅⋅⋅π bonding catalysis represents a novel approach for activating π systems.
  • This catalytic strategy enables efficient cycloaddition reactions with controlled stereoselectivity.
  • Further exploration of chalcogen⋅⋅⋅π interactions in catalysis is warranted.