Copper-Catalyzed Radical Relay 1,3-Carbocarbonylation across Two Distinct CâC Bonds.
Org Lett
; 26(15): 3014-3019, 2024 Apr 19.
Article
em En
| MEDLINE
| ID: mdl-38547326
ABSTRACT
The radical relay provides an effective paradigm for intermolecular assembly to achieve functionalization across remote chemical bonds. Herein, we report the first radical relay 1,3-carbocarbonylation of α-carbonyl alkyl bromides across two separate CâC bonds. The reaction is highly chemo- and regioselective, with two C(sp3)-C(sp3) bonds and one CâO bond formed in a single orchestrated operation. In addition, the synthesis method under mild conditions and using inexpensive copper as the catalyst allows facile access to structurally diverse 1,3-carbocarbonylation products. The plausible mechanism is investigated through a series of control experiments, including radical trapping, radical clock experiments, critical intermediate trapping, and 18O labeling experiment.
Texto completo:
1
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2024
Tipo de documento:
Article
País de afiliação:
China