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Heck reaction with an alkenylidenecyclopropane: the formation of arylallylidenecyclopropanes
Authors:Yacoub Fall  Maurice Santelli
Institution:a Laboratoire de Synthèse Organique, Faculté des Sciences de St-Jérôme, Université d’Aix-Marseille, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France
b Institut Sciences Chimique de Rennes, Université de Rennes ‘Catalyse et Organométalliques’ Campus de Beaulieu, 35042 Rennes, France
Abstract:The palladium-tetraphosphine catalyzed arylation of an alkylidenecyclopropane gives a simple and direct access to 1-aryl-2-methyl-1-(2,2,3,3-tetramethylcyclopropylidene)propenes. This reaction tolerates several functional groups on the aryl bromides. Even heteroaryl bromides have been used successfully. This reaction probably proceeds via a classical oxidative addition of the aryl bromide to palladium, insertion of the Cdouble bond; length as m-dashCMe2 bond in the Ar-Pd bond followed by β-elimination to give the dienes.
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