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Stereoselective Synthesis of Z‑Vinylsilanes via Palladium-Catalyzed Direct Intermolecular Silylation of C(sp2)–H Bonds

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posted on 21.09.2017, 18:00 by Jin-Long Pan, Chao Chen, Zhi-Gang Ma, Jia Zhou, Li-Ren Wang, Shu-Yu Zhang
An efficient and convenient palladium-catalyzed direct intermolecular silylation of C­(sp2)–H bonds by using disilanes as the silicon source with the assistance of a readily removable bidentate directing group is reported. This strategy provided a regio- and stereoselective protocol for exclusive synthesis of Z-vinylsilanes with reasonable to excellent yields and good functional group compatibility. Silylation of the isolated palladacycle intermediate revealed the Z-stereoselective pathway. Moreover, the practicality and effectiveness of this method were illustrated by a gram-scale experiment and further functionalization of the silylation product.

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