Direct C3-H Alkylation and Alkenylation of Quinolines with Enones.
Angew Chem Int Ed Engl
; : e202416451, 2024 Sep 19.
Article
en En
| MEDLINE
| ID: mdl-39297203
ABSTRACT
Conversion of quinoline C-H bonds to C-C bonds is essential for obtaining the enormous array of derivatives required for pharmaceutical and agrochemical development. Despite over a century of synthetic efforts, the direct alkylation and alkenylation at C3-H positions in a wide array of quinoline precursors remain predominantly challenging and elusive. This report outlines the first successful quinoline C3-H alkylation and alkenylation reactions, exhibiting exceptional regio- and stereoselectivity, all achieved under redox-neutral and transition-metal-free conditions. The method involves a three-step, one-pot or two-pot sequence, including 1,4-dearomative addition, functionalization at C3-, elimination or transalkylation to produce 3-alkylated /alkenylated quinolines. The presence of a carbonyl group in these products allows for further synthetic manipulations, enabling the production of cyanides, amides, amines, or simple alkyl derivatives.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Año:
2024
Tipo del documento:
Article
País de afiliación:
China
Pais de publicación:
Alemania