Lightly fluorous [Pd(OAc)2{P(C6H4-p-SiMe2CH2CH2C6F13)3}2] in the methoxycarbonylation of styrene: Formation, performance and stability of the catalyst system

The fluorous palladium(II) complex, [Pd(OAc)2{P(C6H4-p-SiMe2CH2CH2C6F13)3}2], has been prepared and characterized. Its application in the catalytic methoxycarbonylation of styrene in an MeOH/CF3C6H5 mixture (1/1 v/v) has been explored and its activity was compared to that of [Pd(OAc)2(PPh3)2]. The fluorous complex showed a lower activity but a significantly higher selectivity towards the branched product. Investigation of both the conversion-versus-time and i:n ratio-versus-time profiles showed an unusual behaviour in the case of the fluorous complex, which has been ascribed to the formation of a dinuclear species for the fluorous complex.

Graphical abstractThe fluorous complex [Pd(OAc)2{P(C6H4-p-SiMe2CH2CH2C6F13)3}2] was applied in the methoxycarbonylation of styrene. Significant differences in activity, selectivity and stability compared to its non-fluorous analogue were observed. The results are relevant for the development of a fluorous biphasic approach to the recycling of Pd-based alkoxycarbonylation catalysts. Figure optionsDownload full-size imageDownload as PowerPoint slide