TY - JOUR
T1 - Divergent Mechanisms of the Banert Cascade with Propargyl Azides
AU - Alexander, Juliana R.
AU - Packard, Mary H.
AU - Hildebrandt, Alanna M.
AU - Ott, Amy A.
AU - Topczewski, Joseph J.
N1 - Publisher Copyright:
Copyright © 2020 American Chemical Society.
PY - 2020/3/6
Y1 - 2020/3/6
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.9b03061
DO - 10.1021/acs.joc.9b03061
M3 - Article
C2 - 31944764
AN - SCOPUS:85081930181
SN - 0022-3263
VL - 85
SP - 3174
EP - 3181
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 5
ER -