18406-02-5

Upstream product

• 617-86-7 triethylsilane 
• 402-52-8 methyl 4-(trifluoromethyl)phenyl ether 
• 122-46-3 3-acetoxytoluene 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 106-44-5 p-cresol 
• 994-30-9 triethylsilyl chloride 

Relevant academic research and scientific papers

Photocatalyzed cross-dehydrogenative coupling of silanes with alcohols and water

An efficient method for the dehydrogenative coupling of silanes with alcohols under photocatalysis was developed. The reaction proceeded in the presence of Ru(bpy)3Cl2(0.5 mol%) under visible light irradiation in acetonitrile at room temperature. The developed methodology was also applicable for the synthesis of silanols using water as a coupling partner.

Nitrenium Salts in Lewis Acid Catalysis

Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and are extensively employed as donor ligands in coordination chemistry or as nucleophiles in organic chemistry. By contrast, electrophilic nitrogen-containing compounds are much rarer. Nitrenium cations are a new family of nitrogen-based Lewis acids, the reactivity of which remains largely unexplored. In this work, nitrenium ions are explored as catalysts in five organic transformations. These reactions are the first examples of Lewis acid catalysis employing nitrogen as the site of substrate activation. Moreover, these compounds are readily accessed from commercially available reagents and exhibit remarkable stability toward moisture, allowing for benchtop transformations without the need to pretreat solvents.

Hydrodehalogenation of organohalides by Et3SiH catalysed by group 4 metal complexes and B(C6F5)3

Catalytic hydrodehalogenation (HDH) of aliphatic organohalides such as trifluorotoluenes by Et3SiH proceeds in the presence of readily available group 4 metal compounds: Cp′2MX2 (Cp′ = η5-C5H5 or η5-C5Me5; X = F, Cl, or Me; M = Ti, Zr, or Hf), CpTiCl3 and TiCl4 with a catalytic amount of B(C6F5)3. The use of metallocenes in combination with the borane activator leads to a better selectivity of the reaction, i.e., suppression of Friedel-Crafts alkylations of arenes.

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.

Regioselective Iridium-Catalyzed Asymmetric Monohydrogenation of 1,4-Dienes

A highly efficient regio- and enantioselective monohydrogenation of 1,4-dienes has been realized using an iridium catalyst with a chiral N,P-ligand under mild conditions. The substrate scope was studied and included both unfunctionalized as well as functionalized substituents on the meta- or para-position. Substrates having substituents with functionalities such as silyl protected alcohols or ketals were monohydrogenated in high regioselectivity and high enantiomeric excess (up to 98% ee).

Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis

A major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [(C 6F5)3PF][B(C6F5) 4] 1 is shown to catalyze the dehydrocoupling of silanes with amines, thiols, phenols, and carboxylic acids to form the Si-E bond (E = N, S, O) with the liberation of H2 (21 examples). This catalysis, when performed in the presence of a series of olefins, yields the concurrent formation of the products of dehydrocoupling and transfer hydrogenation of the olefin (30 examples). This reactivity provides a strategy for metal-free catalysis of olefin hydrogenations. The mechanisms for both catalytic reactions are proposed and supported by experiment and density functional theory calculations.

An efficient synthesis of silyl ethers of primary alcohols, secondary alcohols, phenols and oximes with a hydrosilane using InBr3 as a catalyst

An efficient method for the preparation of silyl ethers by InBr3 catalyzed silylation of primary alcohols, secondary alcohols, phenols and oxime with a hydrosilane is described.

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

Facile methods for the direct conversions of aryl acetates into the corresponding methoxymethyl ethers or silyl ethers

Direct conversion of aryl acetates into aryl methoxymethyl ethers or aryl trialkylsilyl ethers was readily accomplished by treatment with methoxymethyl bromide or trialkylsilyl trifluoromethanesulfonate, respectively, in the presence of sodium methoxide.

Protection of Hydroxy Groups by Silylation: Use in Peptide Synthesis and as Lipophilicity Modifiers for Peptides

A survey of a series of organosilyl derivatives of serine and tyrosine has shown that they have a satisfactory stability profile for use in peptide synthesis.Only when alkaline conditions were used did side-reactions appear.A range of stability profiles have been determined from a study of organosilyl derivatised dipetides under different conditions, giving t1/2 values for hydrolysis ranging from 41 to 465 min in acid conditions, yet giving long-term stability at pH-values near to neutrality.