Synthesis of Diarylamines via Nitrosonium-Initiated C-N Bond Formation.
J Org Chem
; 89(14): 10316-10326, 2024 Jul 19.
Article
in En
| MEDLINE
| ID: mdl-38950197
ABSTRACT
Electron-rich diarylamines, exemplified by anisole-derived amines, play pivotal roles in process chemistry, pharmaceuticals, and materials. In this study, homo-diarylamines were synthesized directly from the C-H activation of electron-rich arenes by sodium nitrate/trifluoroacetic acid and the successive treatment of iron powder. Mechanistic investigations reveal that nitrosoarene serves as the reaction intermediate, and the formation of the second C-N bond between the resulting nitrosoarene and electron-rich arene is catalyzed by the nitrosonium ion (NO+). Thus, hetero-diarylamines were synthesized using preformed nitrosoarenes and various electron-rich arenes. This reaction complements a range of cross-coupling reactions catalyzed by transition metal catalysts.
Full text:
1
Database:
MEDLINE
Language:
En
Journal:
J Org Chem
Year:
2024
Type:
Article
Affiliation country:
Taiwan