Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles.
J Am Chem Soc
; 130(29): 9613-20, 2008 Jul 23.
Article
en En
| MEDLINE
| ID: mdl-18588302
ABSTRACT
In the cross-coupling reactions of unprotected oxindoles with aryl halides, Pd- and Cu-based catalyst systems displayed orthogonal chemoselectivity. A Pd-dialkylbiarylphosphine-based catalyst system chemoselectively arylated oxindole at the 3 position, while arylation occurred exclusively at the nitrogen using a Cu-diamine-based catalyst system. Computational examination of the relevant L1Pd(Ar)(oxindolate) and diamine-Cu(oxindolate) species was performed to gain mechanistic insight into the controlling features of the observed chemoselectivity.
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Colección:
01-internacional
Base de datos:
MEDLINE
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Idioma:
En
Revista:
J Am Chem Soc
Año:
2008
Tipo del documento:
Article
País de afiliación:
Estados Unidos