Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C–H ac...

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Detalles Bibliográficos
Autores: Cendón Mariño, Borja; Casanova González, Noelia; Comanescu, Cezar; García Fandiño, Rebeca; Seoane Fernández, Andrés; Gulías Costa, Moisés; Mascareñas Cid, José Luis
Tipo de documento: Artículo
Fecha de publicación:2017
País:España
Institución:Universidad de Santiago de Compostela (USC)
Repositorio:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
Lenguaje:Inglés
OAI Identifier:oai:minerva.usc.gal:10347/15444
Acceso en línea:http://hdl.handle.net/10347/15444
Nivel de acceso:Acceso abierto
Palabra clave:Materias::Investigación::23 Química::2302 Bioquímica
Descripción
Sumario:2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C–H activation of the alkenylanilide involves a classical concerted metalation–deprotonation (CMD) mechanism