Open AccessDivergent Mechanisms of the Banert Cascade with Propargyl Azides
Author(s) -
Juliana R. Alexander,
Mary H. Packard,
Alanna M. Hildebrandt,
Amy A. Ott,
Joseph J. Topczewski
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b03061
Subject(s) - cascade , propargyl , sigmatropic reaction , chemistry , substituent , combinatorial chemistry , inflection , computational chemistry , computer science , stereochemistry , organic chemistry , catalysis , artificial intelligence , chromatography
Triazoles are privileged heterocycles for a variety of applications. The synthesis of 1 H -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.