Pyridine–hydrazone ligands in enantioselective palladium-catalyzed Suzuki–Miyaura cross-couplings

The geometries and coordination properties of modular pyridine–hydrazone N,N-ligands containing C-symmetric trans-2,5-diphenylpyrrolidine and trans-2,5-diphenylpiperidine as the terminal dialkylamino units have been analyzed by X-ray diffraction analysis of [PdCl(N,N)] complexes [(N,N)=pyridine hydr...

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Detalles Bibliográficos
Autores: Álvarez-Casao, Yolanda, Estepa, Beatriz, Monge, David, Ros, Abel, Iglesias-Sigüenza, Javier, Álvarez, Eleuterio, Fernández, Rosario, Lassaletta, José M.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/148486
Acceso en línea:http://hdl.handle.net/10261/148486
Access Level:acceso abierto
Palabra clave:N-Ligands
Asymmetric catalysis
Palladium, Biaryls
Cross-coupling
Descripción
Sumario:The geometries and coordination properties of modular pyridine–hydrazone N,N-ligands containing C-symmetric trans-2,5-diphenylpyrrolidine and trans-2,5-diphenylpiperidine as the terminal dialkylamino units have been analyzed by X-ray diffraction analysis of [PdCl(N,N)] complexes [(N,N)=pyridine hydrazone ligand]. In combination with Pd(OAc)as the precatalyst, these ligands provide high enantioselectivities (up to 95:5 er) in asymmetric Suzuki–Miyaura cross couplings of 2-methoxy-1-naphthyl bromides with 1-naphthyl and 2-tolyl boronic acids.