Chan, Daniel G. published the artcileEnol Silyl Ethers via Copper(II)-Catalyzed C-O Bond Formation, Recommanded Product: Triisopropylsilanol, the publication is Organic Letters (2011), 13(10), 2778-2781, database is CAplus and MEDLINE.
Cu(II) acetate catalyzes the coupling of pinacol vinylboronates with silanols producing enol silyl ethers. This represents a novel enol silyl ether synthesis via formation of the C-O bond instead of the conventional Si-O bond. This also constitutes the 1st transition-metal-catalyzed oxidative cross-coupling with silanols. Thirteen enol silyl ethers were prepared by reaction of tert-butyldimethylsilanol with pinacol vinylboronates in the presence of Cu(II) acetate, 3-hexyne, triethylamine, pyridine N-oxide and oxygen in 28% to 72% yield. E.g., reaction of E-PhCH2OCH2CH2CH:CHBpin (HBpin = pinacolborane) with tert-butyldimethylsilanol gave E-PhCH2OCH2CH2CH:CHOSiButMe2 in 72% yield. Direct silylation of a hydroxyketoaldehyde would not be feasible using conventional methods, but reaction of the hydroxy ketoboronate ester E-MeC(O)CH2CH(OH)(CH2)3CH:CHBpin with tert-butyldimethylsilanol afforded E-MeC(O)CH2CH(OH)(CH2)3CH:CHOSiButMe2 in 42% yield.
Organic Letters published new progress about 17877-23-5. 17877-23-5 belongs to alcohols-buliding-blocks, auxiliary class Protection and Derivatization Reagent, name is Triisopropylsilanol, and the molecular formula is C9H22OSi, Recommanded Product: Triisopropylsilanol.
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