Stereoselective Synthesis of Z-Vinylsilanes via Palladium-Catalyzed Direct Intermolecular Silylation of C(sp2)–H Bonds
| Autor: | Jia Zhou, Jin-Long Pan, Li-Ren Wang, Zhi-Gang Ma, Chao Chen, Shu-Yu Zhang |
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| Rok vydání: | 2017 |
| Předmět: |
Denticity
Silylation 010405 organic chemistry Chemistry Organic Chemistry Intermolecular force chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Catalysis Surface modification Organic chemistry Stereoselectivity Physical and Theoretical Chemistry Palladium |
| Zdroj: | Organic Letters. 19:5216-5219 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b02486 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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