Aerobic Fujiwara–Moritani alkenylation and dienylation of ferrocene

Pd(OAc)2-catalyzed aerobic alkenylation and dienylation of ferrocene with electron-poor olefins and dienes (ethyl acrylate, methyl (E)-cinnamate, diethyl fumarate and maleate, ethyl sorbate and sorbic acid) is reported. In the case of acrylate and cinnamate the reaction leads to mixtures of mono- and dialkenylated ferrocenes. In other cases the products of mono alkenylation and dienylation are formed in low yield. The relatively slow (∼1 week) reaction takes place in AcOH solutions at room temperature.

Aerobic ferrocene C–H bond activation/alkenylation catalyzed by Pd(OAc)2.Figure optionsDownload as PowerPoint slideHighlights
► We examine the Fujiwara–Moritani alkenylation and dienylation of ferrocene.
► The reaction proceeds slowly at room temperature and in the presence of air.
► Mixtures of mono- and disubstituted ferrocenes are formed in some cases.
► The products were separated by column chromatography.