Pd(0) and Pd(II) derivatives with heteroannularly bridged chiral ferrocenyl diphosphine ligands - A stereochemical analysis |
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Authors: | M. Carmen Carrió n,Ana Ló pez-Agenjo,Walter Weissensteiner |
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Affiliation: | a Departamento de Química Inorgánica, Orgánica y Bioquímica, IRICA, Universidad de Castilla-La Mancha, Avda. C. J. Cela, 10, 13071 Ciudad Real, Spain b Institut für Organische Chemie, Universität Wien, Währinger Strasse 38, A-1090 Wien, Austria c Department of Chemistry, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria |
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Abstract: | The ligands (Sc, Sp)-1-diphenylphosphino-2,1′-(1-dicyclohexylphosphinopropanediyl)ferrocene, (Sc, Sp)-PPCyPF, and (Sc, Sp)-1-diphenylphosphino-2,1′-(1-diphenylphosphinopropanediyl)ferrocene, (Sc, Sp)-PPPhPF, have been used in the synthesis of the new Pd(0) and Pd(II) derivatives [Pd(PPCyPF)(DMFU)] (1) (DMFU = dimethylfumarate), [Pd(PPCyPF)(MA)] (2) (MA = maleic anhydride), [Pd(η3-2-Me-C3H4)(PP)]OTf (PP = PPCyPF, 3; PPPhPF, 4) (OTf = triflate), [PdRR′(PP)] (R = Me, R′ = Cl, PP = PPCyPF, 5, PPPhPF, 6; R = R′ = Me, PP = PPCyPF, 7, PPPhPF, 8; R = R′ = C6F5, PP = PPCyPF, 9, PPPhPF, 10). The molecular structure of 7 has been determined by X-ray diffraction. In the cases of complexes 1-4 two isomers are formed depending on the orientation of the ancillary ligand with respect to the ferrocenyl core. The stereochemistry of these complexes has been determined. In complex 6 the two possible isomers are obtained whereas in complex 5 the derivative with the Me group trans to PPh2 is selectively formed. Restricted rotation of the pentafluorophenyl groups with respect to the Pd-C bond has been found in 9 and 10. In all derivatives the conformation of the ferrocenyl ligand is the same as that seen by X-ray diffraction and deduced from NMR data. |
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Keywords: | Diphosphines Ferrocenyl ligands Chirality Palladium Stereochemistry |
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