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Homogeneous catalytic aminocarbonylation of iodoalkenes and iodobenzene with amino acid esters under conventional conditions and in ionic liquids |
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| Authors: | Ern? Mü ller,Rita Skoda-Fö ldes,Eszter Taká cs,George Kokotos,Lá szló Kollá r |
| Affiliation: | a Department of Inorganic Chemistry, University of Pécs, PO Box 266, H-7624 Pécs, Hungary b Department of Organic Chemistry, University of Veszprém, H-8200 Veszprém, Hungary c Research Group for Petrochemistry of the Hungarian Academy of Sciences, PO Box 158, H-8201 Veszprém, Hungary d Laboratory of Organic Chemistry, University of Athens, 15771 Athens, Greece e Research Group for Chemical Sensors of the Hungarian Academy of Sciences, H-7624 Pécs, Hungary |
| Abstract: | Amino acid methyl esters were used as amine nucleophiles in palladium catalysed aminocarbonylation of iodobenzene and iodoalkenes (1-iodo-cyclohexene and 17-iodo-androst-16-ene). 2-Oxo-carboxamide type derivatives can be isolated as a result of double CO insertion by using iodobenzene as a substrate at elevated carbon monoxide pressure. On the contrary, carboxamides of expected structure were obtained exclusively in excellent yields in the whole pressure range by using iodoalkenes. The aminocarbonylation of 17-iodo-androst-16-ene in [bmim][PF6] or [bmim][BF4] (where bmim=1-butyl-3-methyl-imidazolium cation) ionic liquids was also carried out and the ionic liquid-catalyst mixtures have been reused several times with only a small loss of activity. |
| Keywords: | Aminocarbonylation Carbon monoxide Amino acid Palladium Ionic liquid |
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