180295-27-6

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 122-97-4 3-Phenyl-1-propanol 
• 321887-70-1 (2-methylallyl )triisopropylsilane 
• 114566-88-0 1-triisopropylsilanyl-1H-imidazole 
• 678187-56-9 triisopropylsilyldiphenylphosphine 
• 742112-05-6 cinnamyloxy(triisopropylsilane) 
• 104-54-1 3-Phenylpropenol 
• 6485-79-6 chlorotriisopropylsilane 
• 104-55-2 3-phenyl-propenal 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 24400-84-8 allyl triisopropylsilane 
• 423171-96-4 1-(triisopropylsilyl)oxy-3-phenyl-2-propene 

Downstream Products

• 112471-51-9 2-(3-phenylpropoxy)tetrahydro-2H-pyran 
• 70770-06-8 1-benzyloxy-3-phenylpropane 
• 104-53-0 3-phenyl-propionaldehyde 
• 42113-39-3 ((3-phenylpropoxy)methylene)dibenzene 
• 122-97-4 3-Phenyl-1-propanol 

Relevant academic research and scientific papers

Breaking C-O Bonds with Uranium: Uranyl Complexes as Selective Catalysts in the Hydrosilylation of Aldehydes

We report herein the possibility to perform the hydrosilylation of carbonyls using actinide complexes as catalysts. While complexes of the uranyl ion [UO2]2+ have been poorly considered in catalysis, we show the potentialities of the Lewis acid [UO2(OTf)2] (1) in the catalytic hydrosilylation of a series of aldehydes. [UO2(OTf)2] proved to be a very active catalyst affording distinct reduction products depending on the nature of the reductant. With Et3SiH, a number of aliphatic and aromatic aldehydes are reduced into symmetric ethers, while iPr3SiH yielded silylated alcohols. Studies of the reaction mechanism led to the isolation of aldehyde/uranyl complexes, [UO2(OTf)2(4-Me2N-PhCHO)3], [UO2(μ-κ2-OTf)2(PhCHO)]n, and [UO2(μ-κ2-OTf)(κ1-OTf)(PhCHO)2]2, which have been fully characterized by NMR, IR, and single-crystal X-ray diffraction.

Tetrahydroxydiboron-Mediated Palladium-Catalyzed Transfer Hydrogenation and Deuteriation of Alkenes and Alkynes Using Water as the Stoichiometric H or D Atom Donor

There are few examples of catalytic transfer hydrogenations of simple alkenes and alkynes that use water as a stoichiometric H or D atom donor. We have found that diboron reagents efficiently mediate the transfer of H or D atoms from water directly onto unsaturated C-C bonds using a palladium catalyst. This reaction is conducted on a broad variety of alkenes and alkynes at ambient temperature, and boric acid is the sole byproduct. Mechanistic experiments suggest that this reaction is made possible by a hydrogen atom transfer from water that generates a Pd-hydride intermediate. Importantly, complete deuterium incorporation from stoichiometric D2O has also been achieved.

Unique Chemoselective Hydrogenation using a Palladium Catalyst Immobilized on Ceramic

A heterogeneous palladium catalyst supported on a ceramic (5 % Pd/ceramic) was developed. The catalyst exhibited a specific chemoselectivity for hydrogenation that has never been achieved by other palladium-catalyzed methods. Either aliphatic or aromatic N-Cbz groups could be deprotected to the corresponding free-amines, while the hydrogenolysis of benzyl esters and ethers did not proceed. Furthermore, aryl chlorides and epoxides were tolerant under the Pd/ceramic-catalyzed hydrogenation conditions. 5 % Pd/ceramic could be reused without any loss of catalyst activity, as no palladium leaching was detected in the reaction media.

Cationic Au(I)- and Pt(II)-catalyzed silylation of alcohols using allylsilanes

The silylation of alcohols using allylsilanes was catalyzed by cationic Au(I) and Pt(II) species, which were prepared in situ from the metal chlorides ([AuCl(PPh3)], PtCl2) and a silver salt. TBS-, TES-, and TIPS-protections of vario

Solvent-modulated Pd/C-catalyzed deprotection of silyl ethers and chemoselective hydrogenation

Recently we have reported undesirable and frequent deprotection of the TBDMS protective group of a variety of hydroxyl functions occurred under neutral and mild hydrogenation conditions using 10% Pd/C in MeOH. The deprotection of silyl ethers is susceptible to significant solvent effect. TBDMS and TES protecting groups were selectively cleaved in the presence of acid-sensitive functional groups such as TIPS ether, TBDPS ether and dimethyl acetal under hydrogenation condition using 10% Pd/C in MeOH. In contrast, chemoselective hydrogenation of reducible functional groups such as acetylene, olefin and benzyl ether, proceeds in the presence of TBDMS or TES ethers in AcOEt or MeCN.

Unexpected deprotection of silyl and THP ethers induced by serious disparity in the quality of Pd/C catalysts and elucidation of the mechanism

Commercial Pd/C catalysts show different catalytic activity toward the deprotection of silyl and THP ethers. The Pd/C purchased from Merck and ACROS exhibits marked tendency to cleave these protective groups unexpectedly without hydrogen conditions although Aldrich's Pd/C (20,569-9) is inactive in the absence of hydrogen. It was proved that the Pd/C disparity toward the deprotection of TES and THP ethers results from residual acids and/or palladium chloride in the production process of Pd/Cs. Although a TES ether cleavage reaction in the absence of hydrogen and a THP ether cleavage reaction in the presence of hydrogen using 10% Pd/C were recently published, we could conclude they were only an acid-catalyzed solvolysis, the acid being released from the catalyst. Hydrogen is essential for the actual 10% Pd/C-catalyzed cleavage of TES ethers and THP ethers which must be stable under the true Pd/C-catalyzed hydrogenation conditions.

Activation of silylphosphines by diethyl azodicarboxylate: Novel silylation of alcohols

A novel activation mode of silylphosphines and an application of that to silylation of alcohols were described. Silylphosphines were found to be instantly activated by means of DEAD and PPTS to form reactive silyl cation equivalents. By using the activate

A remarkable solvent effect toward the Pd/C-catalyzed cleavage of silyl ethers

Selective hydrogenation conditions of olefin, benzyl ether and acetylene functionalities in the presence of TBDMS or TES ether have been developed.

Effective silylation of carboxylic acids under solvent-free conditions with tert-butyldimethylsilyl chloride (TBDMSCL) and triisopropylsilyl chloride (TIPSCL)

Varions types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2°, 3° hydroxyl groups are observed.

Efficient and selective protection of alcohols and phenols with triisopropylsilyl chloride/imidazole using microwave irradiation

A very simple and efficient method is described for silylation of alcohols and phenols using triisopropylsilyl chloride and imidazole under microwave irradiation. High selectivity was observed for silylation of primary and secondary alcohols and also for structurally different phenols. (C) 2000 Published by Elsevier Science Ltd.