Enantio- and Regioselective Electrooxidative Cobalt-Catalyzed C-H/N-H Annulation with Alkenes.
Angew Chem Int Ed Engl
; 62(11): e202218533, 2023 Mar 06.
Article
em En
| MEDLINE
| ID: mdl-36658097
ABSTRACT
In recent years, the merging of electrosynthesis with 3d metal catalyzed C-H activation has emerged as a sustainable and powerful technique in organic synthesis. Despite the impressive advantages, the development of an enantioselective version remains elusive and poses a daunting challenge. Herein, we report the first electrooxidative cobalt-catalyzed enantio- and regioselective C-H/N-H annulation with olefins using an undivided cell at room temperature (up to 99 % ee). t Bu-Salox, a rationally designed Salox ligand bearing a bulky tert-butyl group at the ortho-position of phenol, was found to be crucial for this asymmetric annulation reaction. A strong cooperative effect between t Bu-Salox and 3,4,5-trichloropyridine enabled the highly enantio- and regioselective C-H annulation with the more challenging α-olefins without secondary bond interactions (up to 96 % ee and 97 3 rr). Cyclovoltametric studies, and the preparation, characterization, and transformation of cobaltacycle intermediates shed light on the mechanism of this reaction.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2023
Tipo de documento:
Article
País de afiliação:
China