Synthesis and Evaluation of Azolium-Based Halogen-Bond Donors

Richard A. Squitieri, Keegan P. Fitzpatrick, Ashley A. Jaworski, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

46 Scopus citations


A method for the synthesis of iodinated imidazolium and triazolium N-heterocyclic halogen-bond-donor catalysts has been developed. This approach was applied to the synthesis of a variety of 1,2,4-triazolium salts to prepare a series of novel chiral halogen-bond-donor catalysts. The counterions of the iodinated triazoliums can be readily exchanged with chiral and achiral non-coordinating counterions to produce unique scaffolds. Their ability to promote/catalyse a conjugate addition reaction with indole was investigated. Through these initial studies, a set of general guidelines and considerations for the application of these halogen-bond donors in organocatalysis have been established.

Original languageEnglish (US)
Pages (from-to)10069-10073
Number of pages5
JournalChemistry - A European Journal
Issue number43
StatePublished - Aug 2019


  • Lewis bases
  • azolium
  • catalysis
  • conjugate addition
  • halogen bonding

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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