Ruthenium(II)-Catalyzed C-H (Hetero)Arylation of Alkenylic 1,n-Diazines (n = 2, 3, and 4): Scope, Mechanism, and Application in Tandem Hydrogenations.
J Org Chem
; 83(3): 1462-1477, 2018 02 02.
Article
em En
| MEDLINE
| ID: mdl-29319315
ABSTRACT
A general ruthenium(II)-catalyzed methodology enabling the (hetero)arylation of alkenylic C-H bonds utilizing a series of synthetically appealing diazines as directing groups is presented. Despite the presence of additional nitrogen lone pairs remote from the C-H bond activation site, which could eventually poison the catalyst, the reaction times are short (3 h), thus being suitable for selective double C-H bond arylation. Mixtures of EZ isomeric products were observed in some cases, which were further hydrogenated in a tandem manner in the presence of the remaining ruthenium catalyst from the first step, representing an alternative approach to more difficult C(sp3)-H bond functionalization. According to mechanistic studies, the unexpected EZ product formation seems to occur by thermal CâC bond isomerization after the reductive elimination step.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2018
Tipo de documento:
Article
País de afiliação:
França