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Ramar Arun Kumar1,2, Manas R Pattanayak1, Expédite Yen-Pon1

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Summary

Mesoionic 1,3-dithiolium-4-olates react with alkynes to form thiophenes. This study also discovered their orthogonal reaction with azides for double ligation, creating novel polyaromatic thiophenes.

Keywords:
click chemistrycycloadditionstrained moleculessynthetic methodsthiophenes

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Area of Science:

  • Organic Chemistry
  • Heterocyclic Chemistry

Background:

  • Mesoionic compounds are versatile synthetic intermediates.
  • Thiophene derivatives are important in materials science and medicinal chemistry.

Purpose of the Study:

  • To investigate the reactivity of mesoionic 1,3-dithiolium-4-olates with strained alkynes.
  • To explore the potential for orthogonal reactions with azides.
  • To develop a novel route to polyaromatic thiophenes.

Main Methods:

  • Cycloaddition reactions between mesoionic 1,3-dithiolium-4-olates and strained alkynes.
  • Sequential reactions involving azides for double ligation.

Main Results:

  • Formation of thiophene cycloaddition products.
  • Discovery of orthogonal reactivity with azides enabling double ligation.
  • Development of a divergent synthesis of benzo[c]thiophenes.

Conclusions:

  • Mesoionic 1,3-dithiolium-4-olates are effective dipoles for thiophene synthesis.
  • The discovered orthogonal reactivity provides a new tool for constructing complex molecules.
  • This work offers a novel entry to unconventional polyaromatic thiophenes.