Heck reaction with an alkenylidenecyclopropane: the formation of arylallylidenecyclopropanes |
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Authors: | Yacoub Fall Maurice Santelli |
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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 |
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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 C CMe2 bond in the Ar-Pd bond followed by β-elimination to give the dienes. |
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