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Content available remote Bidentate ligands templated by a convex trimetallic bis(salphen) platform
A Zn3-bis(salphen) compound was used as a template for the construction of bidentate phosphine ligands by self-assembly with phosphines containing a carboxyl group. The convex shape of the template, exposing the three zinc atoms, ensured the correct orientation of the assembled diphosphine, such that it can coordinate to a single metal atom. The strong zinc-carboxylate bond guaranteed the integrity of the final assembly at the low concentrations (1 mM) used in catalysis. Depending on the substitution pattern of the benzoic acid phosphines, either monometallic chelates or dimeric complexes were formed. Coordination studies were carried out for Pt and Rh. A modest chelate effect in the rhodium catalyzed hydroformylation of 1-octene (l/b=4.7) confirmed the formation of the bidentate assemblies.
Rhodium is build into a nano-structured calcium silicate during the synthesis of the silicate. Thereby, it was desired to create a robust heterogeneous catalyst, which does not suffer from catalyst leaching like rhodium impregnated on a pre-formed silicate. While this was achieved, the silicate structure was adversely affected by the incorporation of rhodium - the surface area and pore volume of the material were found to be comparatively low. Alcohol and acid washing were tested to address this issue. The alcohol treatment proved detrimental as catalytic material was leached from the silicate. The acid washed rhodium containing calcium silicate was quite active in the hydroformylation of alkenes and did not suffer loss of catalyst into the product phase. Acid treated rhodium containing silicates were more active than their untreated counterparts but less selective due to access to the rhodium centers being opened. [...]
A first effort employing a range of polar-group functionalized phosphines (L 1 –L 7 ) to design mononuclear Rh(I) compounds of [Rh(quin-8-O)(CO)(L)] (quin-8-O = 8-hydroxy quinolate) is described. The reaction of a Rh(I) precursor [Rh(μ-Cl)(CO)2]2 with 8-hydroxyquinoline in the presence of a base followed by phosphines (L 1 –L 7 ) produced only a single isomer of [Rh(quin-8-O)(CO)(L)] compounds (1–7) with pendant, i.e. non-bonded, polar-groups (includes carboxyl, hydroxyl and formyl). A relationship between Δgd31P chemical shifts and the ν(C≡O) was derived to evaluate and explain the σ-donor properties of these phosphines with respect to the electronic properties of the polar groups and the extent of π-back-bonding to the CO group. These mononuclear Rh(I)-Phosphines were investigated as catalysts in the hydroformylation of 1-hexene and cyclohexene in aqueous two-phase and single-phase solvent systems. The Rh(I) catalysts with strong σ-donor and hydrophilic phosphines provided better yields and selectivities for the hydroformylation products, which is a reverse trend compared to literature reports. When the Rh(I) compounds contained strong σ-donor phosphines, the π-acceptor properties of the pyridine ring of 8-hydroxyquinolate were found to be beneficial for the facile cleavage of the CO group during hydroformylation, and additionally, to improve the kinetic stability of catalysts. [...]
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