High-Precision Catalysts: Regioselective Hydroformylation of Internal Alkenes by Encapsulated Rhodium Complexes
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Abstract:
We report the formation of high-precision catalysts using encapsulated rhodium complexes. In the current example, the encapsulated rhodium catalyst shows unprecedented high selectivity in the rhodium-catalyzed hydroformylation of internal alkenes, forming predominantly one of the branched aldehydes. This catalyst system is the first example that is able to discriminate between carbon atoms C3 and C4 in trans-3-octene.Keywords:
Octene
Alkene
Following the facile synthesis of a novel phosphine oxide compound, (diphenylphosphinoyl)phenylmethanol (1), this compound was employed as a ligand in the rhodium-catalyzed hydroformylation of alkenes, with good conversions and regioselectivities. This ligand was partially resolved using an enzyme, and enantioselective hydroformylation was carried out with the addition of a rhodium(I) complex. The rhodium(I) complex containing ligand 1 was not isolated, although it was subjected to low-temperature NMR studies.
Phosphine oxide
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The hydroformylation of alkenylalkoxysilanes catalyzed by rhodium complexes allows the preparation of aldehyde-functionalized silanes. It is possible to improve the regioselectivity of this reaction by adding an excess of triphenylphoshine and by temperature variation.
Silanes
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Carbonylation
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The present state of art on the application of carbene-rhodium complexes as stable catalysts for hydroformylation reaction is described. A critical analysis of the influence of pressure and temperature on the hydroformylation of non-modified rhodium complexes and those ones described in the presence of carbenes is also done. Finally, a set of experiments using NHCs prepared by us at different reactions conditions is presented and discussed. Keywords: Aliphatic olefins, hydroformylation, rhodium, N-heterocyclic carbene ligands, Rhodium-NHC Complexes, Rhodium-Carbonyl Complexes, Influence of pressure, styrene, Influence of Temperature
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Key words hydroformylation - alkenes - asymmetric synthesis - bisdiazaphospholanes - rhodium
Carbonylation
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The hydroformylation of alkenylalkoxysilanes catalyzed by rhodium complexes allows the preparation of aldehyde-functionalized silanes. It is possible to improve the regioselectivity of this reaction by adding an excess of triphenylphoshine and by temperature variation.
Silanes
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