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Palladium‐Catalyzed Three‐Component Reaction of Dihydrosilanes and Vinyl Iodides in the Presence of Alcohols: Rapid Assembly of Silyl Ethers of Tertiary Silanes
Author(s) -
Yuan Weiming,
Orecchia Patrizio,
Oestreich Martin
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805595
Subject(s) - silylation , silanes , palladium , chemistry , catalysis , iodide , silyl ether , organic chemistry , alkyl , polymer chemistry , methyl iodide , silane
A one‐pot reaction that directly converts dihydrosilanes into silyl ethers of tertiary silanes is reported. Under palladium catalysis, one Si−H bond of the dihydrosilane formally engages in C(sp 3 )−Si bond formation with a vinyl iodide while the other Si−H bond is transformed into a silyl iodide that undergoes facile alcoholysis with an alcohol. The C−C double bond is reduced in that process. This three‐component reaction provides in a single synthetic operation an access to silyl ethers of functionalized and hindered alcohols. Several of those would otherwise be difficult to make but the intermediacy of a highly reactive silyl iodide even allows for tert ‐butanol to react at room temperature.