Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2.
J Am Chem Soc
; 137(25): 8206-18, 2015 Jul 01.
Article
en En
| MEDLINE
| ID: mdl-26027938
A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and ß-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Oxígeno
/
Compuestos Férricos
/
Alquenos
/
Hidrocarburos Aromáticos
Idioma:
En
Revista:
J Am Chem Soc
Año:
2015
Tipo del documento:
Article
Pais de publicación:
Estados Unidos