Palladium-Catalyzed Directed Aldehyde C-H Arylation of Quinoline-8-carbaldehydes: Exploring the Reactivity Differences between Aryl (Pseudo) Halides.
J Org Chem
; 87(24): 16343-16350, 2022 12 16.
Article
in En
| MEDLINE
| ID: mdl-36413613
ABSTRACT
We have developed a method for Pd-catalyzed direct C-H arylation of quinoline-8-carbaldehydes with either aryl iodides or aryl diazonium salts for the synthesis of aryl quinolinyl ketones. Aryl iodide substituted with an electron-donating group favors the reaction, whereas aryl diazonium salt substituted with an electron-withdrawing group showed excellent reactivity. A range of aryl quinolinyl ketones were synthesized in good-to-excellent yields, with very good functional group tolerance. Our methodology was successfully applied to synthesize highly potent tubulin polymerization inhibitors and can be easily scaled up to a gram scale.
Full text:
1
Database:
MEDLINE
Main subject:
Palladium
/
Quinolines
Language:
En
Journal:
J Org Chem
Year:
2022
Type:
Article
Affiliation country:
India