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One-Step Access to Heteroatom-Functionalized Imidazol(in)ium Salts.

Dmitry V PasyukovMaxim A ShevchenkoKonstantin E ShepelenkoOleg V KhazipovJulia V BurykinaEvgeniy G GordeevMikhail E MinyaevVictor M ChernyshevValentine P Ananikov
Published in: Angewandte Chemie (International ed. in English) (2022)
Imidazolium salts have ubiquitous applications in energy research, catalysis, materials and medicinal sciences. Here, we report a new strategy for the synthesis of diverse heteroatom-functionalized imidazolium and imidazolinium salts from easily available 1,4-diaza-1,3-butadienes in one step. The strategy relies on a discovered family of unprecedented nucleophilic addition/cyclization reactions with trialkyl orthoformates and heteroatomic nucleophiles. To probe general areas of application, synthesized N-heterocyclic carbene (NHC) precursors were feasible for direct metallation to give functionalized M/carbene complexes (M=Pd, Ni, Cu, Ag, Au), which were isolated in individual form. The utility of the chloromethyl function for the postmodification of the synthesized salts and Pd/carbene complexes was demonstrated. The obtained complexes and imidazolium salts demonstrated good activities in Pd- or Ni-catalyzed model cross-coupling and C-H activation reactions.
Keyphrases
  • ionic liquid
  • quantum dots
  • room temperature
  • sensitive detection
  • molecularly imprinted
  • visible light
  • high resolution
  • highly efficient
  • mass spectrometry
  • solid phase extraction