18758-56-0

Upstream product

• 60-12-8 2-phenylethanol 
• 789-25-3 HSiPh₃ 
• 96-09-3 styrene oxide 
• 76-86-8 Triphenylsilyl chloride 

Downstream Products

• 60-12-8 2-phenylethanol 
• 18857-43-7 ((benzhydryloxy)triphenylsilane) 
• 76-86-8 Triphenylsilyl chloride 
• 18839-09-3 Si(Oet-2-ph)4 

Relevant academic research and scientific papers

Mild synthesis of silyl ethers: Via potassium carbonate catalyzed reactions between alcohols and hydrosilanes

A method has been developed for the silanolysis of alcohols using an abundant and non-corrosive base K2CO3 as a catalyst. Reactions between a variety of alcohols and hydrosilanes generate silyl ethers under mild conditions. The use of hydrosilanes leads to the formation of H2 as the only byproduct thus avoiding the formation of stoichiometric strong acids. The mild conditions lead to a wide scope of possible alcohol substrates and good functional group tolerance. Selective alcohol silanolysis is also observed in the presence of reactive C-H bonds, lending this method for extensive use in protection group chemistry.

N-Heterocyclic Olefin Catalyzed Silylation and Hydrosilylation Reactions of Hydroxyl and Carbonyl Compounds

N-Heterocyclic olefins (NHOs), the alkylidene derivatives of N-heterocyclic carbenes (NHCs), have recently emerged as a new family of promising organocatalysts with strong nucleophilicity and Br?nsted basicity. The development of a novel method is shown using NHOs as efficient promoters for the direct dehydrogenative silylation of alcohols or hydrosilylation of carbonyl compounds. Preliminary results of the first NHO-promoted asymmetric synthesis are also discussed.

Metal-Free Ammonium Iodide Catalyzed Oxidative Dehydrocoupling of Silanes with Alcohols

An ammonium iodide catalyzed direct oxidative coupling of silanes with alcohols to give various alkoxysilane derivatives was discovered. tert -Butyl hydroperoxide proved to be an efficient oxidant for this transformation. Attractive features of this protocol include its transition-metal-free nature and the mild reaction conditions.

Regioselective hydrosilylation of epoxides catalysed by nickel(II) hydrido complexes

Bench-stable nickel fluoride complexes bearing NNN pincer ligands have been employed as precursors for the regioselective hydrosilylation of epoxides at room temperature. A nickel hydride assisted epoxide opening is followed by the cleavage of the newly formed nickel oxygen bond by σ-bond metathesis with a silane.

N-heterocyclic carbene organocatalysts for dehydrogenative coupling of silanes and hydroxyl compounds

Go organic! N-Heterocyclic carbene (NHC) 1,3-diisopropyl-4,5- dimethylimidazol-2-ylidene (IiPr) has been found to be an efficient and selective catalyst for the dehydrogenative coupling of a wide range of silanes and hydroxyl groups to form Si-O bonds under mild and solvent-free conditions (see scheme). Mechanistic studies indicated that the activation of hydroxyl groups by the NHC is the most plausible initial step for the process. Copyright

Gold(I)-phosphine catalyst for the highly chemoselective dehydrogenative silylation of alcohols

(Chemical Equation Presented) A gold(I) complex of Xantphos AuCl(xantphos) catalyzes the dehydrogenative silylation of alcohols with high chemoselectivity and solvent tolerance. It is selective for the silylation of hydroxyl groups in the presence of alke

Versatile dehydrogenative alcohol silylation catalyzed by Cu(I)-phosphine complex

(Chemical Equation Presented) Cu(I) complexes of xanthane-based diphosphines were versatile catalysts for dehydrogenative alcohol silylation, exhibiting high activity and broad substrate scope. Highly selective silylation of 1-decanol over 2-decanol is possible even with a silylating reagent of small steric demand such as HSiMe2Ph or HSiEt3.

B(C6F5)3-Catalyzed Silation of Alcohols: A Mild, General Method for Synthesis of Silyl Ethers

The commercially available borane tris(pentafluorophenyl)borane, B(C6F5)3, is an effective catalyst for the dehydrogenative silation of alcohols using a variety of silanes, R3SiH, R2SiH2, and R2R′SiH. Generally, the reactions occur in a convenient time frame at room temperature using 2 mol % of the borane and are clean and high yielding, with dihydrogen as the only byproduct. Primary aliphatic alcohols are silated cleanly but slowly, with reaction times ranging from 20 to 144 h. Faster reaction times can be achieved by increasing the catalyst loading to 8 mol % or by heating the reaction to ～60°C. Secondary and tertiary alcohols react more rapidly, with most reactions being complete in 0.5-2 h. The reaction is tolerant of many functional groups including C=C, C=C, -Br, aliphatic ketones, C(O)OR, lactones, furans, OBn, OMe, and NO2; examples of each are given. Using the phenolic substrate 2,4,6-trimethylphenol, a number of different silanes were tested. Only the most bulky silanes (Bn3SiH and Pri3SiH) were not reactive under these conditions. The selectivity of the silation reactions are roughly governed by the relative basicity of the alcohols (and other functions in the molecule) with more basic groups being selectively silated. These observations are rationalized on the basis of a mechanism that invokes borane activation of the silane by hydride abstraction. The resulting intermediate silylium/hydridoborate ion pair then reacts with alcohols to give the observed silyl ether and dihydrogen products.