Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes |
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Authors: | Isabelle KondolffHenri Doucet Maurice Santelli |
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Institution: | Laboratoire de Synthèse Organique associé au CNRS, Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France |
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Abstract: | cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/PdCl(C3H5)]2 efficiently catalyses the Heck reaction of disubstituted alkenes such as methyl crotonate, ethyl cinnamate, methyl methacrylate or α-methylstyrene with a variety of aryl halides. In the presence of 1,2-disubstituted alkenes the stereoselectivities of the reactions strongly depend on the substituents of the alkenes. Selectivities up to 97% in favor of E-isomers can be obtained for the addition to methyl crotonate. With the 1,1-disubstituted alkenes methyl methacrylate or α-methylstyrene mixtures of products are obtained. |
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Keywords: | palladium tetraphosphine Heck reaction disubstituted alkene |
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