Chemoselective activation of sp(3) vs sp(2) C-H bonds with Pd(II).
J Am Chem Soc
; 137(1): 18-21, 2015 Jan 14.
Article
en En
| MEDLINE
| ID: mdl-25423164
ABSTRACT
The first selective coupling of a carbon nucleophile with methyl, ethyl, propyl, and butyl arenes in the absence of a directing group is described. Pd(OAc)2 double C-H activation displays remarkable selectivity for the terminal methyl sites in alkyl arenes, rather than the more commonly observed arene sp(2) C-H activation. Mechanistic studies indicate the intermediacy of an azlactone dimer, obtained from oxidation with Pd(OAc)2, and are consistent with a Pd-catalyzed C-H activation vs a radical process. The observed reactivity establishes that typical reaction solvents (e.g., toluene) can readily participate in C-H activation chemistry.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Compuestos Organometálicos
/
Lactonas
/
Acetatos
Idioma:
En
Año:
2015
Tipo del documento:
Article