Collect. Czech. Chem. Commun. 2007, 72, 453-467

Synthesis, Characterization and Catalytic Utilization of a Ferrocene Diamidodiphosphane

Petr Štěpničkaa,*, Jiří Schulza, Ivana Císařováa and Karla Fejfarováb

a Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic
b Institute of Physics, Academy of Sciences of the Czech Republic, Na Slovance 2, 182 21 Prague 8, Czech Republic


Amidation of 1'-(diphenylphosphanyl)ferrocene-1-carboxylic acid (Hdpf) with ethane-1,2-diamine afforded N,N'-ethylenebis[1'-(diphenylphosphanyl)ferrocene-1-carboxamide] (1), which was isolated in free and solvated form, 1·2AcOH. Both 1 and Hdpf were further converted to their respective phosphane sulfides, 2·2AcOH and 3 that were structurally characterized. Testing of the amidophosphane ligands in Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and various aryl halides revealed that catalyst formed in situ from 1 and palladium(II) acetate is highly active in coupling reactions of aryl bromides whilst the corresponding aryl chlorides showed no or only poor conversions. The catalyst based on 2·2AcOH gave markedly lower yields of the coupling products.

Keywords: Ferrocene; Phosphines; Amides; Suzuki-Miyaura cross-coupling; Crystal structure determination; Ligands; X-Ray diffraction.

References: 44 live references.