Synthesis and Evaluation of Azolium‐Based Halogen‐Bond Donors

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Abstract
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.
Funding Information
  • National Institutes of Health (NIGMS R01-GM073072)

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