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 language | English (US) |
|---|---|
| Pages (from-to) | 3174-3181 |
| Number of pages | 8 |
| Journal | Journal of Organic Chemistry |
| Volume | 85 |
| Issue number | 5 |
| DOIs | |
| State | Published - 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.