Oxone® Mediated Regioselective C(sp2)−H Selenylation and Thiocyanation of Pyrazolo[1,5-a]pyrimidines at Room Temperature

Abhinay S. Chillal, Rajesh T. Bhawale, Umesh A. Kshirsagar

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A mild Oxone® mediated reaction for direct regioselective C−H selenylation and thiocyanation of pyrazolo[1,5-a]pyrimidines is established at ambient temperature. This practical and efficient methodology employs Oxone® as a user friendly, green, non-toxic and cheap reagent to facilitate selenylation and thiocyanation at room temperature. The present method offers high regioselectivity, broad substrate scope, mild conditions and excellent yields. Further, this eco-friendly approach could easily be extended for mild C−H selenylation and thiocyanation of other heterocycles. Mechanistic studies indicate that the reaction occurs through electrophilic substitution mechanism via generation of an electrophilic chalcogen species.

Original languageEnglish
Article numbere202304815
JournalChemistrySelect
Volume9
Issue number1
DOIs
StatePublished - 8 Jan 2024
Externally publishedYes

Keywords

  • Chalcogenation
  • C−H functionalization
  • Heterocycles
  • Pyrazolo[1,5-a]pyrimidines
  • Regioselective

ASJC Scopus subject areas

  • General Chemistry

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