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Download fileStereoselective Synthesis of Z‑Vinylsilanes via Palladium-Catalyzed Direct Intermolecular Silylation of C(sp2)–H Bonds
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posted on 2017-09-21, 18:00 authored by Jin-Long Pan, Chao Chen, Zhi-Gang Ma, Jia Zhou, Li-Ren Wang, Shu-Yu ZhangAn 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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silicon sourcepracticalityvinylsilaneStereoselective SynthesispalladacyclePalladium-Catalyzedgroup compatibilitystrategyIntermolecular Silylationfunctionalizationeffectivenessdisilanegram-scale experimentstereoselective protocolregiopalladium-catalyzedBondstereoselective pathwaysilylation productVinylsilaneyieldmethodbidentatesynthesisassistancebond