C-S-Selective Stille-Coupling Enables Stereodefined Alkene Synthesis.
Angew Chem Int Ed Engl
; : e202408211, 2024 Jul 30.
Article
em En
| MEDLINE
| ID: mdl-39076073
ABSTRACT
A palladium-catalyzed highly CâS-selective Stille cross-coupling between aryl thianthrenium salts and tri- or tetrasubstituted alkenyl stannanes is described. Herein, critical challenges including site- and chemoselectivity control are well addressed through CâH thianthrenation and CâS alkenylation, thereby providing an expedient access to stereodefined tri- and tetrasubstituted alkenes in a stereoretentive fashion. Indeed, the palladium-catalyzed Stille-alkenylation of poly(pseudo)halogenated arenes displays privileged capability to differentiate CâS over CâI, CâBr, CâCl bonds, as well as oxygen-based triflates (CâOTf), tosylates (CâOTs), carbamates and sulfamates under mild reaction conditions. Sequential and multiple cross-couplings via selective CâX functionalization should be widely applicable for increasing functional molecular complexity. Modular installation of stereospecific alkene motifs into pharmaceuticals illustrated the synthetic application of the present protocol in drug discovery.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
China