Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic Enynes

Abstract : 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.
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Submitted on : Monday, October 14, 2013 - 12:35:01 AM
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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, Wiley-VCH Verlag, 2013, 355, pp.3425-3436. ⟨10.1002/adsc.201300746⟩. ⟨hal-00872551⟩

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