Cu-Catalyzed N-Alkynylation of imidazoles, benzimidazoles, indazoles, and pyrazoles using PEG as solvent medium

Glenn Burley, David L Davies, Gerry A Griffith, Michael Lee, Kuldip Singh

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

A facile and efficient Cu(I)-catalyzed cross-coupling method is reported for the preparation of N-alkynyl or N-bromoalkenyl heteroarenes from bromoalkynes.
Generally superior yields and functional group tolerance were obtained with microwave (MW) irradiation using imidazole, benzimidazole, pyrazole, and indazole substrates and poly(ethylene glycol) 400 (PEG400) as an additive.We speculate that PEG400 acts as both a Cu(I)-stabilizing ligand as well as a phase transfer solvent.
Original languageEnglish
Pages (from-to)980-983
Number of pages4
JournalJournal of Organic Chemistry
Volume75
Issue number3
Early online date4 Jan 2010
DOIs
Publication statusPublished - 5 Feb 2010

Keywords

  • phase transfer solvent
  • microwave irradiation
  • bromoalkynes
  • N-alkynyl
  • N-bromoalkenyl heteroarenes

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