Stille reaction over cis-halocyclohexadienediol derivatives |
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Authors: | Viviana Heguaburu,Marcus Mandolesi Sá ,Enrique Pandolfi |
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Affiliation: | a Departamento de Química Orgánica, Facultad de Química, UdelaR, Montevideo, C.P. 11800, Uruguay b Departamento de Química, Universidade Federal de Santa Catarina, Florianópolis, SC 88040-900, Brazil |
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Abstract: | Stille reaction was performed with several halo cis-diol derivatives by reaction with allyltributyltin in the presence of a palladium catalyst forming allyl cis-dihydrodiol derivatives. These couplings were conducted with conventional heating as well as with microwave irradiation. Allylbenzene cis-dihydrodiol was obtained with excellent yield using mild conventional heating. However, if the diol moiety is protected with the isopropylidene group, the expected product is obtained only under microwave irradiation. The unusual reactivity observed for the polyoxygenated derivatives suggests assistance of the free hydroxyls in the catalytic cycle. |
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Keywords: | cis-Cyclohexadienediols Stille reaction Microwave |
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