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10.1021/acs.inorgchem.6b00542
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Título: | C-H Activation in Primary 3-Phenylpropylamines: Synthesis of Seven-Membered Palladacycles through Orthometalation. Stoichiometric Preparation of Benzazepinones and Catalytic Synthesis of Ureas |
Fecha de publicación: | 6-jun-2016 |
Editorial: | ACS |
Cita bibliográfica: | Inorganic Chemistry 2016, 55(11), 5520-5533. |
ISSN: | 5520-5533 |
Materias relacionadas: | CDU::5 - Ciencias puras y naturales::54 - Química::546 - Química inorgánica CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica |
Palabras clave: | Palladacycles Seven-membered Phenylpropylamines CO insertion Catalytic carbonylation Benzazepinones Ureas |
Resumen: | The dimeric cyclometalated complexes [Pd2{C,N-C6H4CH2CH2C(R)(Me)NH2-2}2(µ-Cl)2] (R = Me (1a), H (1b)) are prepared by reacting 1,1-dimethyl-3-phenylpropylammonium or 1-methyl-3-phenylpropylammonium triflate with Pd(OAc)2 in a 1:1 molar ratio, and subsequent treatment with excess NaCl. The mononuclear derivatives [Pd{C,N-C6H4CH2CH2C(R)(Me)NH2-2}Cl(L)] (L = PPh3, R = Me (3a), H (3b); L = 4-picoline (4-pic), R = Me (4a), H (4b)) were prepared from 1a,b, by splitting the chloro-bridges with the neutral ligands L. A conformational analysis of the mononuclear palladacycles in solution has been carried out. Insertion of CO takes place into the Pd–C bond of complexes 1a,b affording Pd(0) and the tetrahydro-benzazepinone 5a or 5b, which possesses potential pharmacological interest. Additionally, the triflate salt A or B undergoes catalytic carbonylation with CO to afford the corresponding N,N’-dialkylurea, using Pd(OAc)2/Cu(OAc)2, in boiling acetonitrile. The crystal structures of 3a·1/2H2O, 3b, 4b·CHCl3, and 5a were determined by X-ray diffraction studies. |
Autor/es principal/es: | Frutos-Pedreño, Roberto García Sánchez, Eva Oliva-Madrid, María José Bautista, Delia Martínez-Viviente, Eloísa Saura-Llamas, Isabel Vicente, José |
Facultad/Departamentos/Servicios: | Facultades, Departamentos, Servicios y Escuelas::Departamentos de la UMU::Química Inorgánica |
Versión del editor: | https://pubs.acs.org/doi/10.1021/acs.inorgchem.6b00542 |
URI: | http://hdl.handle.net/10201/112366 |
DOI: | 10.1021/acs.inorgchem.6b00542 |
Tipo de documento: | info:eu-repo/semantics/article |
Número páginas / Extensión: | 52 |
Derechos: | info:eu-repo/semantics/openAccess Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
Descripción: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Inorganic Chemistry, copyright © American Chemical Society, after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.inorgchem.6b00542 |
Aparece en las colecciones: | Artículos: Química Inorgánica |
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