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Título: | Reactivity toward CO of Eight-Membered Palladacycles Derived from the Insertion of Alkenes into the Pd–C Bond of Cyclopalladated Primary Arylalkylamines of Pharmaceutical Interest. Synthesis of Tetrahydrobenzazocinones, Ortho-Functionalized Phenethylamines, Ureas, and an Isocyanate |
Fecha de publicación: | 16-ago-2012 |
Fecha de defensa / creación: | 2012 |
Editorial: | ACS |
Cita bibliográfica: | Organometallics 2012, 31, 17, 6351–6364 |
ISSN: | Print: 0276-7333 Electronic: 1520-6041 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales CDU::5 - Ciencias puras y naturales::54 - Química |
Palabras clave: | Paladio Paladaciclo Inserción Láquenos |
Resumen: | The ortho-metalated complex [Pd{C,N-C6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (1a) derived from homoveratrylamine reacts with ethyl acrylate, methyl vinyl ketone or 2-norbornene to give the dimeric complex arising from the insertion of the alkene into the Pd–C bond, [Pd{C,N-CH(R)CH2C6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (R = CO2Et (2a1), C(O)Me (2a2)) or [Pd{C,N-CH(C5H8)CHC6H2CH2CH2NH2-2,(OMe)2-4,5}(μ-Br)]2 (2a3). Complexes 2a and the phentermine homologues 2b react with CO to afford Pd(0) and (1) tetrahydrobenzazocinones, the heterocycles resulting from CO insertion into the Pd–C bond and C–N coupling, (2) unnatural aminoacid derivatives resulting from CO insertion and the reaction of the obtained acyl complex with the solvent (MeOH), or the product of protonolysis of the Pd–C bond, depending on the nature of the initial cyclopalladated compound or (3) ureas, alone or mixed with an isocyanate, in the presence of a base. Phentermine derivatives 2b react with HCl to give a dinuclear palladium complex [PdCl(μ- Cl)(L)], where L is the amine arising from the protonolysis of the Pd–C bond or the alkyl group resulting from Pd–N bond protonolysis, depending on the nature of the inserted alkene. The crystal structures of some palladium complexes and organic compounds have been determined by X-ray diffraction studies. |
Autor/es principal/es: | García-López, José-Antonio Oliva-Madrid, María-José Saura-Llamas, Isabel Bautista, Delia Vicente, José |
Director/es: | Vicente, José |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Inorgánica |
Forma parte de: | Compuestos organometálicos y de coordinación funcionalizados. Síntesis y reactividad funcionalizados (CTQ2007-60808/BQU, C-Consolider) |
Versión del editor: | https://pubs.acs.org/doi/10.1021/om300593x |
URI: | http://hdl.handle.net/10201/137374 |
DOI: | https://doi.org/10.1021/om300593x |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 53 |
Derechos: | info:eu-repo/semantics/openAccess Atribución 4.0 Internacional |
Descripción: | This document is made available under the CC-BY 4.0 license http://creativecommons.org/licenses/by /4.0/. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics copyright © American Chemical Society, after peer review and technical editing by the publisher. |
Aparece en las colecciones: | Artículos: Química Inorgánica |
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