Gold versus Palladium: A Regioselective Cycloisomerization of Aromatic EnynesReport as inadecuate

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1 MBCIS - Molécules bioactives, conception, isolement et synthèse 2 DCMR - Laboratoire des mécanismes réactionnels

Abstract : Aromatic enynes can be transformed into arylnaphthalenes or benzofulvenes depending on the reaction conditions. Under goldI catalysis, exclusive or major 6-endo-dig cyclization took place leading to arylnaphthalenes. However, a catalytic system based on palladium iodide-1,3-Bisdiphenylphosphinopropane, 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.

Keywords : aromatic enynes cycloisomerization regioselectivity gold palladium

Author: Jessy Aziz - Gilles Frison - Patrick Le Menez - Jean-Daniel Brion - Abdallah Hamze - Mouad Alami -



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