Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles.
Angew Chem Int Ed Engl
; 60(35): 19207-19213, 2021 08 23.
Article
in En
| MEDLINE
| ID: mdl-34129257
ABSTRACT
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.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Stilbenes
/
Butanols
/
Oxindoles
/
Indoles
/
Nitro Compounds
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2021
Document type:
Article
Affiliation country:
United States