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Divergent Mechanisms of the Banert Cascade with Propargyl Azides.

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.

SUBMITTER: Alexander JR

PROVIDER: S-EPMC7285396 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Divergent Mechanisms of the Banert Cascade with Propargyl Azides.

Alexander Juliana R JR Packard Mary H MH Hildebrandt Alanna M AM Ott Amy A AA Topczewski Joseph J JJ

The Journal of organic chemistry 20200124 5

Triazoles are privileged heterocycles for a variety of applications. The synthesis of 1<i>H</i>-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 dive ...[more]

PMID: 31944764

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