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Upstream product

• 93547-88-7 t-butyl diphenylsilanol 
• 100-51-6 benzyl alcohol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 100-51-6 benzyl alcohol 
• 93547-88-7 t-butyl diphenylsilanol 
• 108-88-3 toluene 
• 1359950-48-3 C₂₃H₂₆OSi 
• 620-47-3 1-methyl-3-(phenylmethyl)-benzene 
• 620-83-7 1-methyl-4-(phenylmethyl)benzene 
• 713-36-0 2-benzyltoluene 

Relevant academic research and scientific papers

A mild method for rapid tert-Butyldiphenylsilylation of primary and secondary alcohols

A rapid and efficient method for the protection of primary and secondary alcohols as their tert-butyldiphenylsilyl (tBDPS) ethers was developed. Reaction of the alcohol and tBDPSCl in DMF with AgNO3, NH4NO3, or NH4ClO4 provides good yields of the corresponding silyl ethers.

Phase-Transfer Catalyzed O-Silyl Ether Deprotection Mediated by a Cyclopropenium Cation

The use of a cyclopropenium cation as a phase-transfer catalyst for O-silyl ether deprotection is reported. Mechanistic insight into this deprotection methodology derived by linear free-energy relationships (LFER), quantum theory of atoms in molecules (QTAIM), and density functional theory (DFT) calculations are also provided.

Amine-free silylation of alcohols under 4-methylpyridine N-oxide-catalyzed conditions

Amine-free silylation of various alcohols catalyzed by 4-methylpyridine N-oxide in the presence of MS4A at room temperature was developed. This simple method gave various silyl ethers in a high yield.

Gold(I)-catalyzed synthesis of unsymmetrical ethers using alcohols as alkylating reagents

A microwave-irradiated alcohol-protecting strategy based on gold catalysis utilizing benzyl alcohol, tert-butyl alcohol and triphenylmethanol as alkylating reagents has been developed. This protecting strategy has wide functional group tolerance with satisfactory yields for the majority of the selected alcohols. The mechanism of this transformation was probed with oxygen-18 isotope labelled alcohols assisted by GC-MS techniques and chemical kinetic experiments. This strategy provides an efficient, straightforward and alternative approach to the preparation of benzyl, tert-butyl and trityl ethers in organic synthesis.

Nonhydrolytic synthesis of silanols by the hydrogenolysis of benzyloxysilanes

The hydrogenolysis of benzyloxysilanes was smoothly catalyzed by Pd/C in THF to give corresponding silanols under nonhydrolytic conditions. The reaction proved to be applicable to various benzyloxysilanes giving silanemonools, diol, and triol.

Metal-free relay oxidation: Valuable synthesis of acylsilane and ketones under aerobic oxidation

In this letter, an example of interesting metal-free relay air oxidation of -hydroxysilanes, promoted by the hydroperoxidated carbonyl compounds derived from the Michael reaction of 5,5-dimethylcyclohexane-1,3-dione and chalcone, is reported. A series of aromatic acylsilanes with TBDPS were obtained in promising isolated yields. In addition, as an extension of the relay oxidation under aerobic conditions, this catalyst-free relay oxidation induced by diketone can be applied to the oxidation of general aromatic alcohols (up to 75% yield). Georg Thieme Verlag Stuttgart · New York.

Selective oxidation of benzylic alcohols and TBDMS ethers to carbonyl compounds with CrO3-H5IO6

Benzyl alcohols and benzyl TBDMS ethers were efficiently oxidized to the corresponding carbonyl compounds in high yield with periodic acid catalyzed by CrO3 at low temperature (-78°C). The oxidation procedure was highly functional group tolerant and very selective for the TBDMS group over the TBDPS group. Georg Thieme Verlag Stuttgart.

Electron-Rich 0 = PR3 compounds: Catalysts for alcohol silylation

The catalytic effect of a group of R3P = O compounds was studied in a mild procedure for the silylation of primary alcohols, secondary alcohols, hindered secondary alcohols, and of hindered phenols in the presence of t-butyldimethylsilyl chlori

Nonionic superbase-catalyzed silylation of alcohols

Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)3N, 1b, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 °C and on rare occasions in DMF from 24 to 80 °C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of lb as a catalyst, tertiary alcohols were recovered unchanged.