Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic Enynes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2013

Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic Enynes

Résumé

Aromatic enynes can be transformed into arylnaphthalenes or benzofulvenes depending on the reaction conditions. Under gold(I) catalysis, exclusive or major 6-endo-dig cyclization took place leading to arylnaphthalenes. However, a catalytic system based on palladium iodide/1,3-Bis(diphenylphosphino)propane, in the presence of cesium carbonate as a base was necessary to furnish exclusively 5-exo-dig cyclization pattern, regardless to the electronic effects of the substituents. In the latter transformation, a mechanistic study (Kinetic Isotopic Effect, Density Functional Theory) involving a C-H activation is suggested for the exclusive benzofulvenes formation.
Fichier principal
Vignette du fichier
manuscript.pdf (425.87 Ko) Télécharger le fichier
Origine : Fichiers produits par l'(les) auteur(s)
Loading...

Dates et versions

hal-00872551 , version 1 (14-10-2013)

Identifiants

Citer

Jessy Aziz, Gilles Frison, Patrick Le Menez, Jean-Daniel Brion, Abdallah Hamze, et al.. Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic Enynes. Advanced Synthesis and Catalysis, 2013, 355, pp.3425-3436. ⟨10.1002/adsc.201300746⟩. ⟨hal-00872551⟩
480 Consultations
342 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More