Counterion Control of t ‐BuO‐Mediated Single Electron Transfer to Nitrostilbenes to Construct N ‐Hydroxyindoles or Oxindoles
In: Angewandte Chemie International Edition, Jg. 60 (2021-07-20), S. 19207-19213
Online
unknown
Zugriff:
tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.
Titel: |
Counterion Control of t ‐BuO‐Mediated Single Electron Transfer to Nitrostilbenes to Construct N ‐Hydroxyindoles or Oxindoles
|
---|---|
Autor/in / Beteiligte Person: | Wink, Donald J. ; Zadrozny, Joseph M. ; Driver, Tom G. ; Zhao, Yingwei ; Sung, Siyoung ; Zhu, Haoran |
Link: | |
Zeitschrift: | Angewandte Chemie International Edition, Jg. 60 (2021-07-20), S. 19207-19213 |
Veröffentlichung: | Wiley, 2021 |
Medientyp: | unknown |
ISSN: | 1521-3773 (print) ; 1433-7851 (print) |
DOI: | 10.1002/anie.202104319 |
Schlagwort: |
|
Sonstiges: |
|