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Selective C-H chalcogenation of thiazoles via thiazol-2-yl-phosphonium salts.

You ZiKonrad WagnerFritz SchömbergIvan Vilotijevic
Published in: Organic & biomolecular chemistry (2021)
Thiazoles and benzothiazoles undergo regioselective C2-H chalcogenation via the sequence of thiazole C2-functionalization with phosphines to produce phosphonium salts which in turn react with S- and Se-centered nucleophiles to give products of C2-H chalcogenation and allow for recovery of the starting phosphine. The atom economical sequence proceeds under mild conditions and features broad scope for both the nucleophiles (electron-rich, electron-poor, sterically hindered thiols) and the various substituted benzothiazoles. The access to the substituted medicinally relevant C2-thio benzothiazoles also enables stereoselectivity improvements in the modified Julia olefinations.
Keyphrases
  • ionic liquid
  • molecular docking
  • electron transfer
  • solar cells
  • fluorescent probe
  • electron microscopy
  • sensitive detection
  • living cells
  • molecular dynamics simulations