Synthesis of Diarylamines via Nitrosonium-Initiated C-N Bond Formation.
J Org Chem
; 89(14): 10316-10326, 2024 Jul 19.
Article
em 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.
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MEDLINE
Idioma:
En
Ano de publicação:
2024
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Article