Imine-palladacycles as phosphine-free precatalysts for low temperature Suzuki-Miyaura synthesis of nucleoside analogues in aqueous media
The synthesis and characterization of new water-soluble dinuclear palladacycles of the general formula [{Pd(R-C^N-SO3Na)(μ-AcO)}2] (R = H (1), OMe (2), Cl (3)) incorporating an ortho-metalated sodium 4-(N-benzylideneamino)benzenesulfonate moiety is reported. These complexes have been revealed to be...
| Autores: | , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2020 |
| País: | España |
| Institución: | Universidad Politécnica de Cartagena(UPCT) |
| Repositorio: | Repositorio Digital UPCT |
| OAI Identifier: | oai:repositorio.upct.es:10317/12880 |
| Acceso en línea: | http://hdl.handle.net/10317/12880 https://pubs.acs.org/doi/10.1021/acs.organomet.0c00580 |
| Access Level: | acceso abierto |
| Palabra clave: | Catalysts Ligands Nucleic acids Palladium Solvents Química Inorgánica 2303 Química Inorgánica |
| Sumario: | The synthesis and characterization of new water-soluble dinuclear palladacycles of the general formula [{Pd(R-C^N-SO3Na)(μ-AcO)}2] (R = H (1), OMe (2), Cl (3)) incorporating an ortho-metalated sodium 4-(N-benzylideneamino)benzenesulfonate moiety is reported. These complexes have been revealed to be excellent phosphine-free catalysts for the synthesis of functionalized nucleoside analogues involving a low-temperature Suzuki–Miyaura coupling of 5-iodo-2′-deoxyuridine with different arylboronic acids in neat water. The potential of 1–3 as synthetic precursors was also tested, and bridging acetates were cleaved by reaction with neutral PPh3, yielding the corresponding mononuclear derivatives [Pd(R-C^N-SO3Na)(AcO)(PPh3)] (R = H (4), MeO (5), Cl (6)). Analytical and spectroscopic techniques confirmed the proposed formulas and reactivities reported for complexes 1–6. Structural characterization by X-ray diffraction of single crystals grown from samples of 4 and 6 produced the unexpected but valuable crystallization-mediated compounds 4cm and 6cm that also supported the results presented here. |
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