Ruthenium(II)-Catalyzed Alkenylation of Ferrocenyl Ketones via C–H Bond Activation

The alkenylation with alkyl acrylates of ferrocenyl alkyl ketones is performed with the [RuCl2(p-cymene)]2 /AgSbF6 catalytic system and leads, via ferrocene C–H bond activation, to moderate yields of the 1,2-disubstituted ferrocene derivatives in the presence of Cu(OAc)2·H2O under aerobic conditions...

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Bibliographic Details
Published in:Organometallics 2012-11, Vol.31 (21), p.7320-7323
Main Authors: Singh, Keisham S, Dixneuf, Pierre H
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
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Summary:The alkenylation with alkyl acrylates of ferrocenyl alkyl ketones is performed with the [RuCl2(p-cymene)]2 /AgSbF6 catalytic system and leads, via ferrocene C–H bond activation, to moderate yields of the 1,2-disubstituted ferrocene derivatives in the presence of Cu(OAc)2·H2O under aerobic conditions at 80–110 °C. The alkenylation of ferrocenyl phenyl ketone, in contrast, takes place at room temperature to afford quantitative yields of the phenyl monoalkenylated product, demonstrating the strong influence of the ferrocenyl group on arene C–H bond functionalization. Small amounts of 2-alkenylferrocenyl 2′-phenyl ketones can also be obtained.
ISSN:0276-7333
1520-6041
DOI:10.1021/om3008162