Tetrahedron

Vinyl tris (trimethylsilyl) silanes: substrates for Hiyama coupling

Z Wang, JP Pitteloud, L Montes, M Rapp, D Derane…

Index: Wang, Zhizhong; Pitteloud, Jean-Philippe; Montes, Lucresia; Rapp, Magdalena; Derane, Djenny; Wnuk, Stanislaw F. Tetrahedron, 2008 , vol. 64, # 22 p. 5322 - 5327

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Citation Number: 16

Abstract

The oxidative treatment of vinyl tris (trimethylsilyl) silanes with hydrogen peroxide in aqueous sodium hydroxide in tetrahydrofuran generates reactive silanol or siloxane species that undergo Pd-catalyzed cross-couplings with aryl, heterocyclic, and alkenyl halides in the presence of Pd (PPh3) 4 and tetrabutylammonium fluoride. Hydrogen peroxide and base are necessary for the coupling to occur while activation of the silanes with fluoride is not ...