Palladium-catalyzed intramolecular carbene insertion into C(sp3)-H bonds

A palladium‐catalyzed carbene insertion into C(sp3)−H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd0 and PdII, is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium‐catalyzed C(sp3)−C(sp3) bon...

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Detalles Bibliográficos
Autores: Solé Arjó, Daniel, Mariani, Francesco, Bennasar Fèlix, M. Lluïsa, Fernández Cadenas, Israel
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/127737
Acceso en línea:https://hdl.handle.net/2445/127737
Access Level:acceso abierto
Palabra clave:Pal·ladi (Element químic)
Catàlisi
Síntesi orgànica
Complexitat computacional
Química organometàl·lica
Palladium
Catalysis
Organic synthesis
Computational complexity
Organometallic chemistry
Descripción
Sumario:A palladium‐catalyzed carbene insertion into C(sp3)−H bonds leading to pyrrolidines was developed. The coupling reaction can be catalyzed by both Pd0 and PdII, is regioselective, and shows a broad functional group tolerance. This reaction is the first example of palladium‐catalyzed C(sp3)−C(sp3) bond assembly starting from diazocarbonyl compounds. DFT calculations revealed that this direct C(sp3)−H bond functionalization reaction involves an unprecedented concerted metalation-deprotonation step.