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Ferrocene phosphinoguanidine donors
Bárta, Ondřej ; Štěpnička, Petr (advisor) ; Dostál, Libor (referee) ; Hoskovcová, Irena (referee)
The "Ferrocene phosphinoguanidine donors" project presented in this Thesis targeted on the synthesis, coordination chemistry and catalytic applications of a rather uncommon class of compounds combining phosphine and guanidine functional groups in their molecules. Two series of such compounds based on ferrocene backbone (henceforth fc = ferrocen-1,1΄-diyl) were studied. Firstly, a reliable synthetic route towards polar phosphinoguanidinium chlorides [R2PfcCH2NHC(NH2)2]Cl, where R = iso-propyl, cyclohexyl, phenyl and 2-furyl, was developed and these ligands were tested as supporting ligands in palladium-catalysed Suzuki-Miyaura-type reactions in biphasic aqueous mixtures and in rhodium-catalysed hydroformylation of 1-hexene. Deduced from the results, the hydrophilic guanidinium tag had a beneficial effect on the catalytic activity and, particularly, the electron-rich phosphines from this series could serve as a useful alternative to commonly used ligands for catalytic applications in polar or aqueous reaction media. Phosphinonitriles R2PfcCN obtained as intermediates during the synthesis of the abovementioned ligands were additionally used for the preparation of the dimeric complexes [Au2(µ-R2PfcCN)2][SbF6]2, in which the gold(I) centre was stabilised by nitrile coordination. These complexes proved...
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