Divergent Mechanisms of the Banert Cascade with Propargyl Azides

Article abstract of DOI:10.1021/acs.joc.9b03061

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.

Full text of DOI:10.1021/acs.joc.9b03061

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Article
Divergent Mechanisms of the Banert Cascade with Propargyl Azides
Juliana R. Alexander, Mary H. Packard, Alanna M. Hildebrandt, Amy A. Ott, and Joseph J Topczewski
J. Org. Chem., Just Accepted Manuscript • DOI: 10.1021/acs.joc.9b03061 • Publication Date (Web): 16 Jan 2020
Downloaded from pubs.acs.org on January 18, 2020
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ACS Paragon Plus Environment

The Journal of Organic Chemistry
G:;9:;%0$%:6!%<.="10'<.=:9:;C:+0%1#B<0%1<.=:C3:CD?D>:
Page 6 of 9
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