Divergent Mechanisms of the Banert Cascade with Propargyl Azides

Juliana R. Alexander, Mary H. Packard, Alanna M. Hildebrandt, Amy A. Ott, Joseph J. Topczewski

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Triazoles are privileged heterocycles for a variety of applications. The synthesis of 1H-triazoles can be accomplished by the Banert cascade from propargylic azides. Depending on the substrate and conditions, the Banert cascade can proceed by either a sigmatropic or prototropic mechanism. This report describes the first detailed kinetic analysis of the Banert cascade proceeding by both pathways including substituent effects and KIE. The analysis identified the inflection point in the divergent pathways, allowing future work to predict which Banert products are accessible.

Original languageEnglish (US)
Pages (from-to)3174-3181
Number of pages8
JournalJournal of Organic Chemistry
Volume85
Issue number5
DOIs
StatePublished - Mar 6 2020

Bibliographical note

Funding Information:
This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award Number R35GM124718. We also acknowledge NIH Shared Instrumentation Grant #S10OD011952. AAO acknowledges support from the University of Minnesota Doctoral Dissertation Fellowship.

Funding Information:
This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award Number R35GM124718. We also acknowledge NIH Shared Instrumentation Grant #S10OD011952. AAO acknowledges support from the University of Minnesota Doctoral Dissertation Fellowship.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

PubMed: MeSH publication types

  • Journal Article
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

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